Refine
Dayang Chem (Hangzhou) Co.,Ltd.
As a leading manufacturer and supplier of chemicals in China, DayangChem not only supply popular chemicals, but also DayangChem's R&D center offer custom synthesis services. DayangChem can provide different quantities of custom synthesis ch
Borrelidin
Cas:7184-60-3
Min.Order:1 Kilogram
FOB Price: $3.0
Type:Lab/Research institutions
inquiryXi'an Xszo Chem Co., Ltd.
1. Factory price and high quality must be guaranteed, base on 8 years of production and R&D experience2. Free samples will be provided,ensure specifications and quality are right for customer3. Customers will receive the most professional technical s
Factory Price API 99% BORRELIDIN 7184-60-3 GMP Manufacturer
Cas:7184-60-3
Min.Order:1 Gram
FOB Price: $0.1
Type:Manufacturers
inquiryZhuozhou Wenxi import and Export Co., Ltd
WITH US,YOUR MONEY IN SAFE,YOUR BUSINESS IN SAFE 1)Quick Response Within 12 hours; 2)Quality Guarantee: All products are strictly tested by our QC, confirmed by QA and approved by third party lab in China, USA, Canada, Germany, UK, Italy, France et
Manufacturer supply CAS 7184-60-3 with best quality
Cas:7184-60-3
Min.Order:1 Kilogram
FOB Price: $139.0 / 210.0
Type:Trading Company
inquiryShanghai Upbio Tech Co.,Ltd
1.In No Less 10 years exporting experience. you can 100% received goods 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Upbio is Specializ
Cyclopentanecarboxylicacid,2-[(2S,4E,6Z,8R,9S,11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl]-,(1R,2R)-
Cas:7184-60-3
Min.Order:1 Gram
Negotiable
Type:Lab/Research institutions
inquiryQingdao Beluga Import and Export Co., LTD
BORRELIDIN CAS:7184-60-3 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality organic intermediates,
BORRELIDIN CAS:7184-60-3
Cas:7184-60-3
Min.Order:1 Gram
Negotiable
Type:Lab/Research institutions
inquiryShandong Hanjiang Chemical Co., Ltd.
Hello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai
Cyclopentanecarboxylicacid,2-[(2S,4E,6Z,8R,9S,11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl]-,(1R,2R)-
Cas:7184-60-3
Min.Order:1 Kilogram
Negotiable
Type:Lab/Research institutions
inquiryHenan Wentao Chemical Product Co., Ltd.
Henan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod
Cyclopentanecarboxylicacid,2-[(2S,4E,6Z,8R,9S,11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl]-,(1R,2R)-
Cas:7184-60-3
Min.Order:0
Negotiable
Type:Lab/Research institutions
inquiryZibo Hangyu Biotechnology Development Co., Ltd
Zibo Hangyu Biotechnology Development Co., Ltd is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemi
TaiChem Taizhou Limited
Established in May 2015, TaiChem Ltd. is initially invested by a British research and development company and started by PhDs back from aboard. The company is registered in China Medical City (CMC), Taizhou, Jiangsu Province, and the production site
Henan Tianfu Chemical Co., Ltd.
Our company was built in 2009 with an ISO certificate.In the past 5 years, we have grown up as a famous fine chemicals supplier in China and we had established stable business relationships with Samsung,LG,Merck,Thermo Fisher Scientific and so on.O
TIANFU-CHEM _ BORRELIDIN 7184-60-3
Cas:7184-60-3
Min.Order:1 Kilogram
Negotiable
Type:Lab/Research institutions
inquirySinoway Industrial Co., Ltd.
Why is SINOWAY:1) Specialized in pharmaceutical and healthcare industrial since 19872) ISO 9001:2015 & SGS audited supplier . 3) Accept various payment terms : T.T 30-60 days.4) We have warehouse in USA with quickly shipment . Application:API
99% up by HPLC BORRELIDIN 7184-60-3
Cas:7184-60-3
Min.Order:0
Negotiable
Type:Trading Company
inquiryHenan Allgreen Chemical Co.,Ltd
high quality Storage:Sealed, dry, microtherm , avoid light and smell. Package:According to the demand of customer Application:Organic synthesis Transportation:by air or by sea
Antimex Chemical Limied
Ansciep Chemical is a professional enterprise manufacturing and distributing fine chemicals and speciality chemicals. We have been dedicated to heterocycle compounds and phenyl rings for tens of years. This is our mature product for export. Our quali
Cyclopentanecarboxylicacid,2-[(2S,4E,6Z,8R,9S,11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl]-,(1R,2R)-
Cas:7184-60-3
Min.Order:0
Negotiable
Type:Lab/Research institutions
inquiryHangzhou Fandachem Co.,Ltd
Borrelidin cas 7184-60-3Appearance:white crystalline powder Storage:Store in dry, dark and ventilated place Package:25KG drum Application:intermediate Transportation:by air, by sea, by express
Shaanxi Cuicheng Biomedical Technology Co., Ltd.
factory?direct?saleAppearance:powder Storage:In cool ,dry place Package:G/bottle; Kg/bag; 2205kg/barrel Application:for pharma use Transportation:Air or sea freight Port:Any main ports of China
Henan Kanbei Chemical Co.,LTD
factory?direct?saleAppearance:White powder Storage:Sealed and preserved Package:200/Kilograms Application:healing drugs Transportation:By sea Port:Shanghai/tianjin
Shanghai Chinqesen Biotechnology Co., Ltd.
Good Quality Package:1kg/bag Application:Medical or chemical Transportation:Air/Train/Sea Port:Shenzhen
Shanghai Yuanye Bio-Technology Co., Ltd.
Known for its best quality and competitve price, this chemicals we offered is widely appreciated by our customers.Appearance:White powder Storage:keep sealed and keep from direct light Package:According client's requirements Application:pharmaceutica
ZHEJIANG JIUZHOU CHEM CO.,LTD
factory?direct?saleAppearance:White powder Storage:Sealed and preserved Package:200/Kilograms Application:healing drugs Transportation:By sea Port:Shanghai/tianjin
Changzhou Extraordinary Pharmatech co.,LTD
Changzhou Extraordinary Pharmatech co., LTD. As a leading chemical manufacturer and supplier in China.DAS authentication is passed.We can provide the popular precursor chemicals, we have our own strong R & D team, have our own laboratories and fa
Hebei youze Biotechnology Co.,Ltd
1: Fast and guaranteed shipment (TNT;EMS;FEDEX;DHL;UPS;EUB, special line) 2: Various payment terms accepted (Btc;MoneyGram;WU) 3: Valued package (Paraffin coating; Double aluminum foil bag; Vacuum packaging) 4: Efficient delivery (3-10 DAYS fast deli
borrelidin CAS:7184-60-3 the cheapest price
Cas:7184-60-3
Min.Order:1 Kilogram
FOB Price: $13.0 / 15.0
Type:Trading Company
inquiryChengdu Push Bio-technology Co., Ltd
Chengdu Push Bio-technology Co., Ltd. provides more than 4,000 natural monomeric substances, including approximately 6,000 products at different grades, specifications and purities. We have specialized in the R&D of medicinally active ingredients sta
Shanghai united Scientific Co.,Ltd.
United Scientific Company Located in Shanghai of China , is a competitive player in the global specialty and fine chemical market. Fenghua has both the expertise and flexibility to produce a wide range of chemicals. Focusing on developing the innovat
Cyclopentanecarboxylicacid,2-[(2S,4E,6Z,8R,9S,11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl]-,(1R,2R)-
Cas:7184-60-3
Min.Order:0
Negotiable
Type:Lab/Research institutions
inquiryA.G. Scientific, Inc.
Description: Borrelidin is a nanomolar angiogenesis inhibitor. Potent angiogenesis inhibitor that induces apoptosis of the capillary tube-forming cell…
Nanjing Raymon Biotech Co., Ltd.
Borrelidin Storage:keep in dry and cool condition Package:25kg or according to cutomer's demand Application:Chemical research/pharma intermediate Transportation:By Sea,by Air,By courier like DHL or Fedx. Port:Shanghai/Shenzhen
Hebei Ruishun Trade Co.,Ltd
Supply top quality products with a reasonable price Application:api
Synthetic route
-
-
631919-63-6
(1'R,1S,2S,2'R,8R,9S,11R,13S,15S,16S)-2-(7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-oxacyclooctadeca-4,6-dien-2-yl)-cyclopentane-1'-carboxylic acid 2-trimethylsilanyl-ethyl ester
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; for 2h; | 94% |
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| With dimethylboron bromide In dichloromethane at -78℃; for 1h; |
-
-
768395-41-1
(1R,2R)-2-((4E,6Z)-(2S,9S,11R,13S,15S,16S)-7-Cyano-16-hydroxy-9,11,13,15-tetramethyl-8,18-dioxo-oxacyclooctadeca-4,6-dien-2-yl)-cyclopentanecarboxylic acid
-
A
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| With sodium tetrahydroborate; cerium(III) chloride In methanol at 0℃; for 1h; Luche reaction; Title compound not separated from byproducts; |
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| With pyridine hydrogenfluoride In tetrahydrofuran at 20℃; for 48h; | 5.2 mg |
| With pyridine; pyridine hydrogenfluoride In tetrahydrofuran at 20℃; for 48h; | 5.20 mg |
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 28 steps 1.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 2.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 3.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 4.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 5.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 6.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 7.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 8.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 9.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 10.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 11.1: Et3N / benzene / 1 h / 20 °C 12.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 13.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 14.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 15.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 15.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 16.1: DMAP / pentane / 168 h / 20 °C 16.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 17.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 18.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 19.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 20.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 21.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 22.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 23.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 24.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 25.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 26.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 27.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 28.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 27 steps 1.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 2.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 3.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 4.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 5.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 6.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 7.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 8.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 9.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 10.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 11.1: Et3N / benzene / 1 h / 20 °C 12.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 13.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 14.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 15.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 15.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 16.1: DMAP / pentane / 168 h / 20 °C 16.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 17.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 18.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 19.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 20.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 21.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 22.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 23.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 24.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 25.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 26.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 27.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 20 steps 1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 2: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 3: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 4: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 5: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 6: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 7: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 8: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 9: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 10: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 11: Et3N / benzene / 1 h / 20 °C 12: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 13: 93 percent / PPTS / ethanol / 10 h / 50 °C 14: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 15: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 16: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 17: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 18: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 19: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 20: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 22 steps 1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 2: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 3: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 4: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 5: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 6: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 7: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 8: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 9: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 10: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 11: Et3N / benzene / 1 h / 20 °C 12: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 13: 93 percent / PPTS / ethanol / 10 h / 50 °C 14: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 15: 19 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 16: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 17: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 18: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 19: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 20: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 21: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 22: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
714973-96-3
(2S,4R,8S,Z)-9-(tert-butyldiphenylsilyloxy)-2,4,6,8-tetramethylnon-3-en-1-ol
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 25 steps 1.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 2.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 3.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 4.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 5.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 6.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 7.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 8.1: Et3N / benzene / 1 h / 20 °C 9.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 10.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 11.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 12.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 12.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 13.1: DMAP / pentane / 168 h / 20 °C 13.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 14.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 15.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 16.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 17.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 18.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 19.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 20.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 21.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 22.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 23.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 24.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 25.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 24 steps 1.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 2.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 3.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 4.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 5.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 6.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 7.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 8.1: Et3N / benzene / 1 h / 20 °C 9.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 10.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 11.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 12.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 12.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 13.1: DMAP / pentane / 168 h / 20 °C 13.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 14.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 15.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 16.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 17.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 18.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 19.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 20.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 21.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 22.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 23.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 24.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 17 steps 1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 2: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 3: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 4: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 5: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 6: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 7: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 8: Et3N / benzene / 1 h / 20 °C 9: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 10: 93 percent / PPTS / ethanol / 10 h / 50 °C 11: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 12: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 13: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 14: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 15: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 16: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 17: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 19 steps 1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 2: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 3: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 4: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 5: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 6: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 7: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 8: Et3N / benzene / 1 h / 20 °C 9: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 10: 93 percent / PPTS / ethanol / 10 h / 50 °C 11: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 12: 19 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 13: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 14: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 15: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 16: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 17: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 18: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 19: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
935872-55-2
C42H66O6SiNCOCF3
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 8 steps 1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 3: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 4: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 5: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 6: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 7: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 8: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
935872-03-0
(3S,4S,6S,8R,10S)-((S,3E,5Z)-7-allyloxy-6-bromo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-oxohepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-4,6,8,10-tetramethyl-11-oxoundecanoate
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 14 steps 1.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 1.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 2.1: DMAP / pentane / 168 h / 20 °C 2.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 3.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 4.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 5.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 6.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 7.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 8.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 9.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 10.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 11.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 12.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 13.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 14.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 13 steps 1.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 1.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 2.1: DMAP / pentane / 168 h / 20 °C 2.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 3.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 4.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 5.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 6.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 7.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 8.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 9.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 10.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 11.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 12.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 13.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
935872-04-1
(S,2Z,4E)-allyl 2-bromo-7-(tert-butyldimethylsilyloxy)-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-dienoate
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 18 steps 1.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 2.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 3.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 4.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 5.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 5.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 6.1: DMAP / pentane / 168 h / 20 °C 6.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 7.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 8.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 9.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 10.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 11.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 12.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 13.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 14.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 15.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 16.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 17.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 18.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 17 steps 1.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 2.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 3.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 4.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 5.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 5.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 6.1: DMAP / pentane / 168 h / 20 °C 6.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 7.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 8.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 9.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 10.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 11.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 12.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 13.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 14.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 15.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 16.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 17.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
935872-05-2
(S,2Z,4E)-allyl 2-bromo-7-hydroxy-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-dienoate
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 17 steps 1.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 2.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 3.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 4.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 4.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 5.1: DMAP / pentane / 168 h / 20 °C 5.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 6.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 7.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 8.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 9.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 10.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 11.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 12.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 13.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 14.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 15.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 16.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 17.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 16 steps 1.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 2.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 3.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 4.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 4.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 5.1: DMAP / pentane / 168 h / 20 °C 5.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 6.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 7.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 8.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 9.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 10.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 11.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 12.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 13.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 14.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 15.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 16.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
935872-06-3
(3S,4S,6S,8R,10S)-((S,3E,5Z)-7-(allyloxy)-6-bromo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-oxohepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-4,6,8,10-tetramethyl-11-(tetrahydro-2H-pyran-2-yloxy)undecanoate
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 16 steps 1.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 2.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 3.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 3.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 4.1: DMAP / pentane / 168 h / 20 °C 4.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 5.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 6.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 7.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 8.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 9.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 10.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 11.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 12.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 13.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 14.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 15.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 16.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 15 steps 1.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 2.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 3.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 3.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 4.1: DMAP / pentane / 168 h / 20 °C 4.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 5.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 6.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 7.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 8.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 9.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 10.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 11.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 12.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 13.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 14.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 15.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
935872-07-4
(3S,4S,6S,8R,10S)-((S,3E,5Z)-7-(allyloxy)-6-bromo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-oxohepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-11-hydroxy-4,6,8,10-tetramethylundecanoate
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 15 steps 1.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 2.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 2.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 3.1: DMAP / pentane / 168 h / 20 °C 3.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 4.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 5.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 6.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 7.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 8.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 9.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 10.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 11.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 12.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 13.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 14.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 15.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 14 steps 1.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 2.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 2.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 3.1: DMAP / pentane / 168 h / 20 °C 3.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 4.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 5.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 6.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 7.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 8.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 9.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 10.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 11.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 12.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 13.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 14.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 13 steps 1.1: DMAP / pentane / 168 h / 20 °C 1.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 2.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 3.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 4.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 5.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 6.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 7.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 8.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 9.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 10.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 11.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 12.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 13.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 12 steps 1.1: DMAP / pentane / 168 h / 20 °C 1.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 2.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 3.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 4.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 5.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 6.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 7.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 8.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 9.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 10.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 11.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 12.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
935872-09-6
(2S,4E,6E,8S,9S,11R,13S,15S,16S)-allyl 16-(tert-butyldimethylsilyloxy)-8-hydroxy-2-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-diene-7-carboxylate
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 12 steps 1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 2: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 3: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 4: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 5: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 6: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 7: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 8: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 9: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 10: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 11: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 12: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 11 steps 1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 2: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 3: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 4: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 5: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 6: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 7: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 8: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 9: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 10: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 11: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
935872-10-9
(2S,4E,6E,8S,9S,11R,13S,15S,16S)-allyl 8,16-bis(tert-butyldimethylsilyloxy)-2-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-diene-7-carboxylate
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 11 steps 1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 2: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 3: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 4: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 5: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 6: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 7: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 8: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 9: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 10: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 11: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 10 steps 1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 2: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 3: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 4: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 5: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 6: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 7: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 8: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 9: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 10: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
935872-12-1
(2S,4E,6E,8S,9S,11R,13S,15S,16S)-16-(tert-butyldimethylsilyloxy)-2-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-diene-7-carboxylic acid
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 10 steps 1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 2: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 3: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 4: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 5: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 6: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 7: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 8: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 9: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 10: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 9 steps 1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 2: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 3: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 4: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 5: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 6: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 7: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 8: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 9: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
935872-13-2
(2S,4E,6E,8S,9S,11R,13S,15S,16S)-16-(tert-butyldimethylsilyloxy)-2-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-diene-7-carboxamide
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 9 steps 1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 2: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 3: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 4: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 5: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 6: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 7: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 8: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 9: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 8 steps 1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 3: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 4: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 5: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 6: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 7: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 8: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
57287-24-8
((1R,2R)-cyclopentane-1,2-diyl)dimethanol
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 26 steps 1.1: NaH / dimethylformamide / -20 - 20 °C 2.1: 6.24 g / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 3.1: 54 percent / tetrahydrofuran / 0.5 h / -78 °C 4.1: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 5.1: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 6.1: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 7.1: 73 percent / benzene / 48 h / 80 °C 8.1: 84 percent / benzene / 39 h / 70 °C 9.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 10.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 11.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 12.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 13.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 13.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 14.1: DMAP / pentane / 168 h / 20 °C 14.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 15.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 16.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 17.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 18.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 19.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 20.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 21.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 22.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 23.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 24.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 25.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 26.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 25 steps 1.1: NaH / dimethylformamide / -20 - 20 °C 2.1: 6.24 g / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 3.1: 54 percent / tetrahydrofuran / 0.5 h / -78 °C 4.1: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 5.1: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 6.1: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 7.1: 73 percent / benzene / 48 h / 80 °C 8.1: 84 percent / benzene / 39 h / 70 °C 9.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 10.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 11.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 12.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 13.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 13.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 14.1: DMAP / pentane / 168 h / 20 °C 14.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 15.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 16.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 17.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 18.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 19.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 20.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 21.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 22.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 23.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 24.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 25.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 18 steps 1: NaH / dimethylformamide / -20 - 20 °C 2: 6.24 g / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 3: 54 percent / tetrahydrofuran / 0.5 h / -78 °C 4: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 5: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 6: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 7: 73 percent / benzene / 48 h / 80 °C 8: 96 percent / DBU; LiCl / acetonitrile / 2 h / 0 °C 9: 94 percent / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C 10: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 11: 93 percent / PPTS / ethanol / 10 h / 50 °C 12: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 13: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 14: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 15: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 16: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 17: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 18: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
90270-02-3, 97937-36-5
(2R,4S)-1-hydroxy-2,4-dimethylpentyl acetate
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 34 steps 1.1: 98 percent / imidazole / CH2Cl2 / 0.5 h / 20 °C 2.1: 98 percent / K2CO3; MeOH / 2 h / 20 °C 3.1: imidazole / dimethylformamide / 0 - 20 °C 4.1: 4.19 g / PPTS; EtOH / 7 h / 50 °C 5.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 6.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 6.2: tetrahydrofuran; hexane / 1 h / -30 °C 6.3: tetrahydrofuran; hexane / -20 °C 7.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 8.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 9.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 10.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 11.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 12.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 13.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 14.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 15.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 16.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 17.1: Et3N / benzene / 1 h / 20 °C 18.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 19.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 20.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 21.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 21.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 22.1: DMAP / pentane / 168 h / 20 °C 22.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 23.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 24.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 25.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 26.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 27.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 28.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 29.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 30.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 31.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 32.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 33.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 34.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 33 steps 1.1: 98 percent / imidazole / CH2Cl2 / 0.5 h / 20 °C 2.1: 98 percent / K2CO3; MeOH / 2 h / 20 °C 3.1: imidazole / dimethylformamide / 0 - 20 °C 4.1: 4.19 g / PPTS; EtOH / 7 h / 50 °C 5.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 6.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 6.2: tetrahydrofuran; hexane / 1 h / -30 °C 6.3: tetrahydrofuran; hexane / -20 °C 7.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 8.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 9.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 10.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 11.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 12.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 13.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 14.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 15.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 16.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 17.1: Et3N / benzene / 1 h / 20 °C 18.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 19.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 20.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 21.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 21.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 22.1: DMAP / pentane / 168 h / 20 °C 22.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 23.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 24.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 25.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 26.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 27.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 28.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 29.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 30.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 31.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 32.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 33.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 26 steps 1.1: 98 percent / imidazole / CH2Cl2 / 0.5 h / 20 °C 2.1: 98 percent / K2CO3; MeOH / 2 h / 20 °C 3.1: imidazole / dimethylformamide / 0 - 20 °C 4.1: 4.19 g / PPTS; EtOH / 7 h / 50 °C 5.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 6.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 6.2: tetrahydrofuran; hexane / 1 h / -30 °C 6.3: tetrahydrofuran; hexane / -20 °C 7.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 8.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 9.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 10.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 11.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 12.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 13.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 14.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 15.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 16.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 17.1: Et3N / benzene / 1 h / 20 °C 18.1: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 19.1: 93 percent / PPTS / ethanol / 10 h / 50 °C 20.1: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 21.1: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 22.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 23.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 24.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 25.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 26.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
147782-80-7
(2S,4R)-5-(tert-butyl(dimethyl)silyloxy)-2,4-dimethyl-1-pentanol
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 32 steps 1.1: imidazole / dimethylformamide / 0 - 20 °C 2.1: 4.19 g / PPTS; EtOH / 7 h / 50 °C 3.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 4.2: tetrahydrofuran; hexane / 1 h / -30 °C 4.3: tetrahydrofuran; hexane / -20 °C 5.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 6.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 7.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 8.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 9.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 10.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 11.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 12.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 13.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 14.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 15.1: Et3N / benzene / 1 h / 20 °C 16.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 17.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 18.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 19.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 19.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 20.1: DMAP / pentane / 168 h / 20 °C 20.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 21.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 22.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 23.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 24.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 25.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 26.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 27.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 28.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 29.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 30.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 31.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 32.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 31 steps 1.1: imidazole / dimethylformamide / 0 - 20 °C 2.1: 4.19 g / PPTS; EtOH / 7 h / 50 °C 3.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 4.2: tetrahydrofuran; hexane / 1 h / -30 °C 4.3: tetrahydrofuran; hexane / -20 °C 5.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 6.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 7.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 8.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 9.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 10.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 11.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 12.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 13.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 14.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 15.1: Et3N / benzene / 1 h / 20 °C 16.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 17.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 18.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 19.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 19.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 20.1: DMAP / pentane / 168 h / 20 °C 20.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 21.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 22.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 23.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 24.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 25.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 26.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 27.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 28.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 29.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 30.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 31.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 24 steps 1.1: imidazole / dimethylformamide / 0 - 20 °C 2.1: 4.19 g / PPTS; EtOH / 7 h / 50 °C 3.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 4.2: tetrahydrofuran; hexane / 1 h / -30 °C 4.3: tetrahydrofuran; hexane / -20 °C 5.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 6.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 7.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 8.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 9.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 10.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 11.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 12.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 13.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 14.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 15.1: Et3N / benzene / 1 h / 20 °C 16.1: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 17.1: 93 percent / PPTS / ethanol / 10 h / 50 °C 18.1: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 19.1: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 20.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 21.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 22.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 23.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 24.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
157837-64-4
(2R,4S)-5-{[tert-butyl(diphenyl)silyl]oxy}-2,4-dimethylpentan-1-ol
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 30 steps 1.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 2.2: tetrahydrofuran; hexane / 1 h / -30 °C 2.3: tetrahydrofuran; hexane / -20 °C 3.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 4.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 5.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 6.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 7.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 8.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 9.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 10.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 11.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 12.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 13.1: Et3N / benzene / 1 h / 20 °C 14.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 15.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 16.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 17.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 17.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 18.1: DMAP / pentane / 168 h / 20 °C 18.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 19.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 20.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 21.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 22.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 23.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 24.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 25.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 26.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 27.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 28.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 29.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 30.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 29 steps 1.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 2.2: tetrahydrofuran; hexane / 1 h / -30 °C 2.3: tetrahydrofuran; hexane / -20 °C 3.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 4.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 5.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 6.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 7.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 8.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 9.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 10.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 11.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 12.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 13.1: Et3N / benzene / 1 h / 20 °C 14.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 15.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 16.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 17.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 17.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 18.1: DMAP / pentane / 168 h / 20 °C 18.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 19.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 20.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 21.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 22.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 23.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 24.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 25.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 26.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 27.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 28.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 29.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 22 steps 1.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 2.2: tetrahydrofuran; hexane / 1 h / -30 °C 2.3: tetrahydrofuran; hexane / -20 °C 3.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 4.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 5.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 6.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 7.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 8.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 9.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 10.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 11.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 12.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 13.1: Et3N / benzene / 1 h / 20 °C 14.1: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 15.1: 93 percent / PPTS / ethanol / 10 h / 50 °C 16.1: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 17.1: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 18.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 19.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 20.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 21.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 22.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
157837-65-5
(2R,4S)-5-{[tert-butyl(diphenyl)silyl]oxy}-2,4-dimethylpentanal
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 29 steps 1.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 1.2: tetrahydrofuran; hexane / 1 h / -30 °C 1.3: tetrahydrofuran; hexane / -20 °C 2.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 3.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 4.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 5.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 6.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 7.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 8.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 9.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 10.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 11.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 12.1: Et3N / benzene / 1 h / 20 °C 13.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 14.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 15.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 16.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 16.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 17.1: DMAP / pentane / 168 h / 20 °C 17.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 18.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 19.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 20.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 21.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 22.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 23.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 24.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 25.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 26.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 27.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 28.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 29.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 28 steps 1.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 1.2: tetrahydrofuran; hexane / 1 h / -30 °C 1.3: tetrahydrofuran; hexane / -20 °C 2.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 3.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 4.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 5.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 6.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 7.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 8.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 9.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 10.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 11.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 12.1: Et3N / benzene / 1 h / 20 °C 13.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 14.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 15.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 16.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 16.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 17.1: DMAP / pentane / 168 h / 20 °C 17.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 18.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 19.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 20.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 21.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 22.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 23.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 24.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 25.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 26.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 27.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 28.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 21 steps 1.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 1.2: tetrahydrofuran; hexane / 1 h / -30 °C 1.3: tetrahydrofuran; hexane / -20 °C 2.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 3.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 4.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 5.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 6.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 7.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 8.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 9.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 10.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 11.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 12.1: Et3N / benzene / 1 h / 20 °C 13.1: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 14.1: 93 percent / PPTS / ethanol / 10 h / 50 °C 15.1: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 16.1: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 17.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 18.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 19.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 20.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 21.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
335060-49-6
(2S,4R)-5-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2,4-dimethylpentyl acetate
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 33 steps 1.1: 98 percent / K2CO3; MeOH / 2 h / 20 °C 2.1: imidazole / dimethylformamide / 0 - 20 °C 3.1: 4.19 g / PPTS; EtOH / 7 h / 50 °C 4.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 5.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 5.2: tetrahydrofuran; hexane / 1 h / -30 °C 5.3: tetrahydrofuran; hexane / -20 °C 6.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 7.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 8.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 9.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 10.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 11.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 12.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 13.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 14.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 15.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 16.1: Et3N / benzene / 1 h / 20 °C 17.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 18.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 19.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 20.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 20.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 21.1: DMAP / pentane / 168 h / 20 °C 21.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 22.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 23.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 24.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 25.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 26.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 27.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 28.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 29.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 30.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 31.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 32.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 33.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 32 steps 1.1: 98 percent / K2CO3; MeOH / 2 h / 20 °C 2.1: imidazole / dimethylformamide / 0 - 20 °C 3.1: 4.19 g / PPTS; EtOH / 7 h / 50 °C 4.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 5.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 5.2: tetrahydrofuran; hexane / 1 h / -30 °C 5.3: tetrahydrofuran; hexane / -20 °C 6.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 7.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 8.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 9.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 10.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 11.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 12.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 13.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 14.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 15.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 16.1: Et3N / benzene / 1 h / 20 °C 17.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 18.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 19.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 20.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 20.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 21.1: DMAP / pentane / 168 h / 20 °C 21.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 22.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 23.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 24.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 25.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 26.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 27.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 28.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 29.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 30.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 31.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 32.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 25 steps 1.1: 98 percent / K2CO3; MeOH / 2 h / 20 °C 2.1: imidazole / dimethylformamide / 0 - 20 °C 3.1: 4.19 g / PPTS; EtOH / 7 h / 50 °C 4.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 5.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 5.2: tetrahydrofuran; hexane / 1 h / -30 °C 5.3: tetrahydrofuran; hexane / -20 °C 6.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 7.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 8.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 9.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 10.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 11.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 12.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 13.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 14.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 15.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 16.1: Et3N / benzene / 1 h / 20 °C 17.1: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 18.1: 93 percent / PPTS / ethanol / 10 h / 50 °C 19.1: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 20.1: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 21.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 22.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 23.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 24.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 25.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
714974-00-2
(1R,2R)-2-(((4-methoxybenzyl)oxy)methyl)cyclopentane-1-carbaldehyde
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 24 steps 1.1: 54 percent / tetrahydrofuran / 0.5 h / -78 °C 2.1: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 3.1: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 4.1: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 5.1: 73 percent / benzene / 48 h / 80 °C 6.1: 84 percent / benzene / 39 h / 70 °C 7.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 8.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 9.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 10.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 11.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 11.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 12.1: DMAP / pentane / 168 h / 20 °C 12.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 13.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 14.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 15.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 16.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 17.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 18.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 19.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 20.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 21.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 22.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 23.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 24.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 23 steps 1.1: 54 percent / tetrahydrofuran / 0.5 h / -78 °C 2.1: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 3.1: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 4.1: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 5.1: 73 percent / benzene / 48 h / 80 °C 6.1: 84 percent / benzene / 39 h / 70 °C 7.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 8.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 9.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 10.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 11.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 11.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 12.1: DMAP / pentane / 168 h / 20 °C 12.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 13.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 14.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 15.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 16.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 17.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 18.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 19.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 20.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 21.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 22.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 23.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 16 steps 1: 54 percent / tetrahydrofuran / 0.5 h / -78 °C 2: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 3: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 4: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 5: 73 percent / benzene / 48 h / 80 °C 6: 96 percent / DBU; LiCl / acetonitrile / 2 h / 0 °C 7: 94 percent / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C 8: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 9: 93 percent / PPTS / ethanol / 10 h / 50 °C 10: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 11: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 12: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 13: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 14: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 15: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 16: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
714974-24-0
((1R,2R)-2-(((4-methoxybenzyl)oxy)methyl)cyclopentyl)methanol
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 25 steps 1.1: 6.24 g / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 2.1: 54 percent / tetrahydrofuran / 0.5 h / -78 °C 3.1: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 4.1: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 5.1: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 6.1: 73 percent / benzene / 48 h / 80 °C 7.1: 84 percent / benzene / 39 h / 70 °C 8.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 9.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 10.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 11.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 12.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 12.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 13.1: DMAP / pentane / 168 h / 20 °C 13.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 14.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 15.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 16.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 17.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 18.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 19.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 20.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 21.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 22.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 23.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 24.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 25.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 24 steps 1.1: 6.24 g / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 2.1: 54 percent / tetrahydrofuran / 0.5 h / -78 °C 3.1: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 4.1: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 5.1: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 6.1: 73 percent / benzene / 48 h / 80 °C 7.1: 84 percent / benzene / 39 h / 70 °C 8.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 9.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 10.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 11.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 12.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 12.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 13.1: DMAP / pentane / 168 h / 20 °C 13.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 14.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 15.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 16.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 17.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 18.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 19.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 20.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 21.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 22.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 23.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 24.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 17 steps 1: 6.24 g / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 2: 54 percent / tetrahydrofuran / 0.5 h / -78 °C 3: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 4: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 5: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 6: 73 percent / benzene / 48 h / 80 °C 7: 96 percent / DBU; LiCl / acetonitrile / 2 h / 0 °C 8: 94 percent / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C 9: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 10: 93 percent / PPTS / ethanol / 10 h / 50 °C 11: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 12: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 13: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 14: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 15: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 16: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 17: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
714973-98-5
(2R,4S,6R,8S)-2,4,6,8-tetramethyl-9-(tetrahydro-2H-pyran-2-yloxy)nonanal
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 21 steps 1.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 2.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 3.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 4.1: Et3N / benzene / 1 h / 20 °C 5.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 6.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 7.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 8.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 8.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 9.1: DMAP / pentane / 168 h / 20 °C 9.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 10.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 11.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 12.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 13.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 14.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 15.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 16.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 17.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 18.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 19.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 20.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 21.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 20 steps 1.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 2.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 3.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 4.1: Et3N / benzene / 1 h / 20 °C 5.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 6.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 7.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 8.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 8.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 9.1: DMAP / pentane / 168 h / 20 °C 9.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 10.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 11.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 12.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 13.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 14.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 15.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 16.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 17.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 18.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 19.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 20.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 13 steps 1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 2: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 3: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 4: Et3N / benzene / 1 h / 20 °C 5: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 6: 93 percent / PPTS / ethanol / 10 h / 50 °C 7: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 8: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 9: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 10: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 11: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 12: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 13: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
714974-01-3
(+)-(S)-1-((1R,2R)-2-((4-methoxybenzyloxy)methyl)cyclopentyl)but-3-en-1-ol
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 23 steps 1.1: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 2.1: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 3.1: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 4.1: 73 percent / benzene / 48 h / 80 °C 5.1: 84 percent / benzene / 39 h / 70 °C 6.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 7.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 8.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 9.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 10.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 10.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 11.1: DMAP / pentane / 168 h / 20 °C 11.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 12.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 13.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 14.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 15.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 16.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 17.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 18.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 19.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 20.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 21.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 22.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 23.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 22 steps 1.1: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 2.1: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 3.1: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 4.1: 73 percent / benzene / 48 h / 80 °C 5.1: 84 percent / benzene / 39 h / 70 °C 6.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 7.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 8.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 9.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 10.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 10.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 11.1: DMAP / pentane / 168 h / 20 °C 11.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 12.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 13.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 14.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 15.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 16.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 17.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 18.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 19.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 20.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 21.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 22.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 15 steps 1: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 2: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 3: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 4: 73 percent / benzene / 48 h / 80 °C 5: 96 percent / DBU; LiCl / acetonitrile / 2 h / 0 °C 6: 94 percent / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C 7: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 8: 93 percent / PPTS / ethanol / 10 h / 50 °C 9: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 10: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 11: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 12: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 13: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 14: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 15: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
714974-13-7
(-)-(2S,4S,6R,8S)-2,4,6,8-tetramethyl-9-(tetrahydro-2H-pyran-2-yloxy)nonan-1-ol
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 22 steps 1.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 2.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 3.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 4.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 5.1: Et3N / benzene / 1 h / 20 °C 6.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 7.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 8.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 9.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 9.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 10.1: DMAP / pentane / 168 h / 20 °C 10.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 11.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 12.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 13.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 14.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 15.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 16.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 17.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 18.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 19.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 20.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 21.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 22.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 21 steps 1.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 2.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 3.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 4.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 5.1: Et3N / benzene / 1 h / 20 °C 6.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 7.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 8.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 9.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 9.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 10.1: DMAP / pentane / 168 h / 20 °C 10.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 11.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 12.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 13.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 14.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 15.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 16.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 17.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 18.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 19.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 20.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 21.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 14 steps 1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 2: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 3: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 4: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 5: Et3N / benzene / 1 h / 20 °C 6: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 7: 93 percent / PPTS / ethanol / 10 h / 50 °C 8: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 9: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 10: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 11: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 12: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 13: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 14: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
714974-16-0
(1'R,2'R,3S)-3-(tert-butyldimethylsilyloxy)-3-[2'-(4''-methoxybenzyloxymethyl)cyclopentyl]propanal
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 20 steps 1.1: 73 percent / benzene / 48 h / 80 °C 2.1: 84 percent / benzene / 39 h / 70 °C 3.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 4.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 5.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 6.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 7.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 7.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 8.1: DMAP / pentane / 168 h / 20 °C 8.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 9.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 10.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 11.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 12.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 13.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 14.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 15.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 16.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 17.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 18.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 19.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 20.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 19 steps 1.1: 73 percent / benzene / 48 h / 80 °C 2.1: 84 percent / benzene / 39 h / 70 °C 3.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 4.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 5.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 6.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 7.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 7.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 8.1: DMAP / pentane / 168 h / 20 °C 8.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 9.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 10.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 11.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 12.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 13.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 14.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 15.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 16.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 17.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 18.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 19.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 12 steps 1: 73 percent / benzene / 48 h / 80 °C 2: 96 percent / DBU; LiCl / acetonitrile / 2 h / 0 °C 3: 94 percent / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C 4: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 5: 93 percent / PPTS / ethanol / 10 h / 50 °C 6: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 7: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 8: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 9: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 10: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 11: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 12: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
714974-15-9
tert-butyl(((S)-1-((1R,2R)-2-(((4-methoxybenzyl)oxy)methyl)cyclopentyl)but-3-en-1-yl)oxy)dimethylsilane
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 22 steps 1.1: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 2.1: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 3.1: 73 percent / benzene / 48 h / 80 °C 4.1: 84 percent / benzene / 39 h / 70 °C 5.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 6.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 7.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 8.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 9.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 9.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 10.1: DMAP / pentane / 168 h / 20 °C 10.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 11.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 12.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 13.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 14.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 15.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 16.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 17.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 18.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 19.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 20.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 21.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 22.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 21 steps 1.1: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 2.1: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 3.1: 73 percent / benzene / 48 h / 80 °C 4.1: 84 percent / benzene / 39 h / 70 °C 5.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 6.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 7.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 8.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 9.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 9.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 10.1: DMAP / pentane / 168 h / 20 °C 10.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 11.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 12.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 13.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 14.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 15.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 16.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 17.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 18.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 19.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 20.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 21.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 14 steps 1: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 2: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 3: 73 percent / benzene / 48 h / 80 °C 4: 96 percent / DBU; LiCl / acetonitrile / 2 h / 0 °C 5: 94 percent / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C 6: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 7: 93 percent / PPTS / ethanol / 10 h / 50 °C 8: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 9: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 10: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 11: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 12: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 13: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 14: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
Conditions
| Conditions | Yield |
|---|---|
| With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; | 96% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: piperazine In dichloromethane at 20℃; | 96% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: morpholine In dichloromethane at 20℃; | 96% |
Conditions
| Conditions | Yield |
|---|---|
| With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; | 93% |
Conditions
| Conditions | Yield |
|---|---|
| With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane | 91% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: 1-phenylmethylpiperazine In dichloromethane at 20℃; | 90% |
Conditions
| Conditions | Yield |
|---|---|
| With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; | 89% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: piperidine In dichloromethane at 20℃; | 89% |
Conditions
| Conditions | Yield |
|---|---|
| With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; | 88% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: 2-(aminoethyl)pyridine In dichloromethane at 20℃; | 88% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 2-Hydroxymethylpyridine In tetrahydrofuran at 20℃; | 88% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: 1-methyl-piperazine In dichloromethane at 20℃; | 87% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: 4-Methoxyphenethylamine In dichloromethane at 20℃; | 87% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: 2-(5-methoxyindol-3-yl)ethylamine In dichloromethane at 20℃; | 86% |
Conditions
| Conditions | Yield |
|---|---|
| With toluene-4-sulfonic acid Reflux; | 85% |
Conditions
| Conditions | Yield |
|---|---|
| With triethylamine; isobutyl chloroformate In tetrahydrofuran at 20℃; | 85% |
-
-
38212-30-5
1-(4-methoxyphenyl)piperazine
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: 4-(4-methoxyphenyl)piperazine In dichloromethane at 20℃; | 85% |
-
-
39536-61-3
N-butylpentylamine
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: N-butylpentylamine In dichloromethane at 20℃; | 85% |
-
-
23032-21-5
D-leucine methyl ester
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: D-leucine methyl ester In dichloromethane at 20℃; | 85% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 1-piperidinoethanol In tetrahydrofuran at 20℃; | 85% |
Conditions
| Conditions | Yield |
|---|---|
| With triethylamine; isobutyl chloroformate In tetrahydrofuran at 20℃; | 84% |
-
-
622-40-2
2-(morpholin-4-yl)ethanol
-
-
7184-60-3
borrelidin
-
-
322480-23-9
2-morpholinoethyl (1R,2R)-2-[(2S,4E,6Z,8R,9S,11R,13S, 15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylate
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 2-(morpholin-4-yl)ethanol In tetrahydrofuran at 20℃; | 83% |
| With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane | 73% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: pyrrolidine In dichloromethane at 20℃; | 83% |
Conditions
| Conditions | Yield |
|---|---|
| In methanol; toluene at 20℃; | 82% |
Conditions
| Conditions | Yield |
|---|---|
| With triethylamine; isobutyl chloroformate In tetrahydrofuran at 20℃; | 82% |
Conditions
| Conditions | Yield |
|---|---|
| With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In tetrahydrofuran at 20℃; for 0.5h; | 81% |
-
-
108-01-0
2-(N,N-dimethylamino)ethanol
-
-
7184-60-3
borrelidin
-
-
1429308-13-3
2-(dimethylamino)ethyl (1R,2R)-2-[(2S,4E,6Z,8R,9S, 11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetra-methyl-18-oxooxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylate
Conditions
| Conditions | Yield |
|---|---|
| With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane | 81% |
| Stage #1: borrelidin With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 2-(N,N-dimethylamino)ethanol In tetrahydrofuran at 20℃; |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: 1-(2-hydroxyethyl)piperazine In dichloromethane at 20℃; | 80% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 2-phenylethanol In tetrahydrofuran at 20℃; | 80% |
Related products
Hot Products
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View