English name:Rivastigmine tartrate Molecular formula : C18H28N2O8 Molecular weight : 400.4235 cas: 129101-54-8 Synonyms: SDZ-ENA 713;ENA 713;ENA-713;Rivastigmine hydrogentartrate;UNII-9IY2357JPE;Carbamic acid, ethylme
Jinlan Pharm-Drugs Technology Co.,Limited (with its export company Hangzhou Royall Import & Export Co.,Ltd.)is located in Hangzhou, Zhejiang Province. Neighboring Ningbo port, Shanghai port, Hangzhou Xiaoshan Int’l Airport and Shanghai Pu
Manufacturer supply Trabectedin CAS 114899-77-3 with attractive price Company profile Wuhan Fortuna Chemical Co.,Ltd established in 2006, is a big integrative chemical enterprise being engaged in Pharmaceutical & its intermediates, Food/Feed
Cas:114899-77-3
Min.Order:10 Kilogram
FOB Price: $10.0
Type:Trading Company
inquiryDayangchem’s R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. Near 20 years DayangChem has provided dif
Cas:114899-77-3
Min.Order:1 Kilogram
FOB Price: $1.0
Type:Lab/Research institutions
inquiryOur main production base is located in Xuzhou industry park. We are certified both to the ISO 9001 and ISO 14001 Standards, have a safety management system in place.Our R&D team masters core technology for process-design of target building block
Our advantages: 1. All inquiries will be replied within 12 hours. 2. Dedication to quality, supply & service. 3. Strictly on selecting raw materials. 4. Reasonable & competitive price, fast lead time. 5. Sample is available for your eva
Cas:114899-77-3
Min.Order:1 Kilogram
FOB Price: $9.0 / 99.0
Type:Trading Company
inquiryWITH 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
Cas:114899-77-3
Min.Order:1 Kilogram
FOB Price: $139.0 / 210.0
Type:Trading Company
inquiry1. Guaranteed purity; 2. Large quantity in stock; 3. Largest manufacturer; 4. Best service after shipment with email; 5. High quality & competitive price; Appearance:White Crystalline Powder Storage:Store in sealed conta
Cas:114899-77-3
Min.Order:10 Gram
Negotiable
Type:Other
inquiryHanways chempharm is a specialized company concentrating on the R&D, production, marketing and technical service of APIs and pharmaceutical intermediates. The marketing department is located in Wuhan. We have two GMP facilities in Hubei Pr
Cas:114899-77-3
Min.Order:1 Kilogram
FOB Price: $200.0 / 400.0
Type:Trading Company
inquiryecteinascidin 743 CAS:114899-77-3 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 interm
Cas:114899-77-3
Min.Order:1 Gram
Negotiable
Type:Lab/Research institutions
inquiryHello, 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
Cas:114899-77-3
Min.Order:1 Kilogram
Negotiable
Type:Lab/Research institutions
inquiryAdvantage : LIDE PHARMACEUTICALS LTD. is a mid-small manufacturing-type enterprise, engaged in pharmaceutical intermediates of R&D, custom-made and production, and also involving trading chemicals for export. We have established the R&
Cas:114899-77-3
Min.Order:0
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Type:Lab/Research institutions
inquiryHenan 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
Cas:114899-77-3
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Type:Lab/Research institutions
inquiryQuick Details ProName:Trabectedin CasNo:114899-77-3 Molecular Formula:C39H43N3O11S Appearance:white powder Application:pharmaceutics DeliveryTime:10 days PackAge:1g/bottle Port:shanghai ProductionCapacity:50 Gram/Month Purity:99% Storage
Cas:114899-77-3
Min.Order:1 Gram
Negotiable
Type:Lab/Research institutions
inquiryOur company provides one-stop services of research - development - production for a variety of special prouducts. Not only do we make effective use of our strong technological strength, but also establish of cooperative relations with several well-
Cas:114899-77-3
Min.Order:100 Milligram
Negotiable
Type:Lab/Research institutions
inquiryCompany Introduction 1. Established in 2005, with two independent business divisions: Fine chemicals division; Pharmaceutical division. 2. Main product: Optical brightener Textile auxiliary Dye stuff Pigments
1. Product advantages: exquisite appearance and unique functions. 2. Product Advantages: Our products are the best,fast speed ,in large stock 3. High-quality products and thoughtful service are your greatest satisfaction. 4. The product
114899-77-3 ecteinascidin 743 Appearance:white powder Storage:room temperature Package:according to customers' requirements Application:Pharma intermediates Transportation:By air(EMS or EUB or FedEx or TNT ect...) or by sea(FOB or CIF or CNF ect..
J&H CHEM R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. J&H CHEM has some Manufacturing base in Jia
Cas:114899-77-3
Min.Order:0
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Type:Lab/Research institutions
inquiryZibo 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
Cas:114899-77-3
Min.Order:10 Gram
FOB Price: $100.0
Type:Lab/Research institutions
inquiryChemvon Biotechnology Co. Ltd., established in the end of 2004, is a high-technology pharmaceutical and fine chemical company in R&D, manufacturing and sales of Trabectedin. With the experience and specialization in technology of asymmetric sy
Cas:114899-77-3
Min.Order:1 Gram
Negotiable
Type:Lab/Research institutions
inquiryOur 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
Cas:114899-77-3
Min.Order:1 Metric Ton
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Type:Lab/Research institutions
inquiryProduct name: Trabectedin CAS No.:114899-77-3 Molecule Formula:C39H43N3O11S Molecule Weight:761.83 Purity: 99.0% Package: 25kg/drum Description:White crystalline powder Manufacture Standards:Enterprise Standard TESTING ITEMS
Cas:114899-77-3
Min.Order:1 Kilogram
Negotiable
Type:Lab/Research institutions
inquiryProduct Details Grade: pharmaceutical grade Purity:99%+ ProductionCapacity: 1000 Kilogram/Month Scope of use: For scientific research only(The product must be used legally) Our Advantage 1. Best quality with competitive price. 2. Quick shipping,
Cas:114899-77-3
Min.Order:1 Gram
Negotiable
Type:Lab/Research institutions
inquiryGMP standard, high purity, competitive price, in stock 1. Quick Response: within 6 hours after receiving your email. 2. Quality Guarantee: All products are strictly tested by our QC, confirmed by QA, and approved by a third-party lab in China, USA,
1. ASMF/US DMF is available. 2. GMP is available. Hangzhou Huarong Pharm Co., Ltd. established since 2009 , has been always focusing on supplying products and services to our clients in the field of small molecule drug. Huarong Pharm has bu
Cas:114899-77-3
Min.Order:1 Kilogram
FOB Price: $99.0
Type:Lab/Research institutions
inquiryfactory?direct?saleAppearance:White Powder Storage:Store In Dry, Cool And Ventilated Place Package:25kg/drum, also according to the clients requirement Application:It is widely used as a thickener, emulsifier and stabilizer Transportation:By Sea Or B
Cas:114899-77-3
Min.Order:1 Kilogram
FOB Price: $18.0 / 20.0
Type:Trading Company
inquiryShandong Mopai Biotechnology 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 chemicals. W
Cas:114899-77-3
Min.Order:1 Gram
Negotiable
Type:Lab/Research institutions
inquiry1.Applied in food field.it can improve the immune system and prolong life. 2.Appliedin cosmetic field.it can improve the skin care. 3.Applied in pharmaceutical field.it can treat various dieases. 4.Our product quality assurance will make our customer
Cas:114899-77-3
Min.Order:1 Metric Ton
FOB Price: $1.5
Type:Trading Company
inquiryProduct Name: ecteinascidin 743 Assay: 99.0% Cas No.: 114899-77-3 Drugs for unresectable or specific advanced soft tissue sarcomas Appearance:Detailed see specif
Cas:114899-77-3
Min.Order:1 Milligram
Negotiable
Type:Lab/Research institutions
inquiry(1'R,6R,6aR,7R,13S,14R,16R)-5-(acetyloxy)-3',4',6,6a,7,13,14,16-octahydro-6',8-dihydroxy-7',9-dimethoxy-4,10,23-trimethyl-19-oxo-spiro[6,16-(epithiopropanoxymethano)-7,13-imino-12H-1,3-dioxolo[7,8]isoquino[3,2-b][3]benzazocine-20,1'(2'H)-isoquinoline]-14-carbonitrile
ecteinascidin 743
Conditions | Yield |
---|---|
With silver nitrate In water; acetonitrile at 20℃; for 11h; | 96.9% |
With silver nitrate In water; acetonitrile at 20℃; for 24h; Inert atmosphere; | 95% |
With water; copper(l) chloride In tetrahydrofuran at 23℃; for 24h; Inert atmosphere; Darkness; | 94% |
Conditions | Yield |
---|---|
Multistep reaction.; |
ethyl 2-bromo-2-(6-(methoxymethoxy)-7-methylbenzo[d][1,3]dioxol-4-yl)acetate
ecteinascidin 743
Conditions | Yield |
---|---|
Multi-step reaction with 20 steps 1.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C 2.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C 3.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C 4.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C 5.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C 6.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C 7.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 8.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C 9.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C 10.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C 11.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C 12.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C 13.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 14.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 15.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 16.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 17.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 18.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 18.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 18.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 19.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 20.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme |
ethyl 2-hydroxy-2-(6-(methoxymethoxy)-7-methylbenzo[d][1,3]dioxol-4-yl)acetate
ecteinascidin 743
Conditions | Yield |
---|---|
Multi-step reaction with 21 steps 1.1: 91 percent / benzotriazole; thionyl bromide / CH2Cl2 / 0.33 h / 20 °C 2.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C 3.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C 4.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C 5.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C 6.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C 7.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C 8.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 9.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C 10.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C 11.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C 12.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C 13.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C 14.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 15.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 16.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 17.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 18.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 19.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 19.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 19.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 20.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 21.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme |
hydroxy-(7-hydroxy-6-methoxymethoxy-benzo[1,3]dioxol-4-yl)-acetic acid ethyl ester
ecteinascidin 743
Conditions | Yield |
---|---|
Multi-step reaction with 23 steps 1.1: 95 percent / K2CO3 / dimethylformamide / 1 h / 23 °C 2.1: 93 percent / K3PO4; Pd(PPh3)4 / dioxane / 4 h / 100 °C 3.1: 91 percent / benzotriazole; thionyl bromide / CH2Cl2 / 0.33 h / 20 °C 4.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C 5.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C 6.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C 7.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C 8.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C 9.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C 10.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 11.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C 12.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C 13.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C 14.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C 15.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C 16.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 17.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 18.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 19.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 20.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 21.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 21.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 21.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 22.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 23.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme |
hydroxy-(6-methoxymethoxy-7-trifluoromethanesulfonyloxy-benzo[1,3]dioxol-4-yl)-acetic acid ethyl ester
ecteinascidin 743
Conditions | Yield |
---|---|
Multi-step reaction with 22 steps 1.1: 93 percent / K3PO4; Pd(PPh3)4 / dioxane / 4 h / 100 °C 2.1: 91 percent / benzotriazole; thionyl bromide / CH2Cl2 / 0.33 h / 20 °C 3.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C 4.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C 5.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C 6.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C 7.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C 8.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C 9.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 10.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C 11.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C 12.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C 13.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C 14.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C 15.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 16.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 17.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 18.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 19.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 20.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 20.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 20.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 21.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 22.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme |
(R)-4-((1R,3S)-8-Hydroxy-3-hydroxymethyl-7-methoxy-6-methyl-1,2,3,4-tetrahydro-isoquinolin-1-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
ecteinascidin 743
Conditions | Yield |
---|---|
Multi-step reaction with 24 steps 1.1: 88 percent / aq. NaHCO3 / CH2Cl2 / 2 h / 20 °C 2.1: 86 percent / Cs2CO3; CsI / dimethylformamide / 3 h / 20 °C 3.1: 92 percent / pyridine; DMAP / CH2Cl2 / 1 h / 20 °C 4.1: 72 percent / trfifluoroacetic acid / CH2Cl2 / 4 h / 20 °C 5.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C 6.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C 7.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C 8.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C 9.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C 10.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C 11.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 12.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C 13.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C 14.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C 15.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C 16.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C 17.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 18.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 19.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 20.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 21.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 22.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 22.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 22.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 23.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 24.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme |
(1R,3S)-3-Acetoxymethyl-8-allyloxy-1-((R)-1-amino-2-hydroxy-ethyl)-7-methoxy-6-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid allyl ester
ecteinascidin 743
Conditions | Yield |
---|---|
Multi-step reaction with 20 steps 1.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C 2.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C 3.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C 4.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C 5.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C 6.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C 7.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 8.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C 9.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C 10.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C 11.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C 12.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C 13.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 14.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 15.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 16.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 17.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 18.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 18.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 18.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 19.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 20.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme |
1-(3-tert-butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-8-hydroxy-3-hydroxymethyl-7-methoxy-6-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid allyl ester
ecteinascidin 743
Conditions | Yield |
---|---|
Multi-step reaction with 23 steps 1.1: 86 percent / Cs2CO3; CsI / dimethylformamide / 3 h / 20 °C 2.1: 92 percent / pyridine; DMAP / CH2Cl2 / 1 h / 20 °C 3.1: 72 percent / trfifluoroacetic acid / CH2Cl2 / 4 h / 20 °C 4.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C 5.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C 6.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C 7.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C 8.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C 9.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C 10.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 11.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C 12.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C 13.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C 14.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C 15.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C 16.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 17.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 18.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 19.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 20.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 21.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 21.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 21.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 22.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 23.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme |
8-allyloxy-1-(3-tert-butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-3-hydroxymethyl-7-methoxy-6-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid allyl ester
ecteinascidin 743
Conditions | Yield |
---|---|
Multi-step reaction with 22 steps 1.1: 92 percent / pyridine; DMAP / CH2Cl2 / 1 h / 20 °C 2.1: 72 percent / trfifluoroacetic acid / CH2Cl2 / 4 h / 20 °C 3.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C 4.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C 5.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C 6.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C 7.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C 8.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C 9.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 10.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C 11.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C 12.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C 13.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C 14.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C 15.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 16.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 17.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 18.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 19.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 20.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 20.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 20.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 21.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 22.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme |
3-acetoxymethyl-8-allyloxy-1-(3-tert-butoxycarbonyl-2,2-dimethyl-oxazolidin-4-yl)-7-methoxy-6-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid allyl ester
ecteinascidin 743
Conditions | Yield |
---|---|
Multi-step reaction with 21 steps 1.1: 72 percent / trfifluoroacetic acid / CH2Cl2 / 4 h / 20 °C 2.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C 3.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C 4.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C 5.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C 6.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C 7.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C 8.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 9.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C 10.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C 11.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C 12.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C 13.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C 14.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 15.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 16.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 17.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 18.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 19.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 19.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 19.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 20.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 21.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme |
C32H35N3O9
ecteinascidin 743
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C 2.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 3.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 4.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 5.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 6.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 7.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 7.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 7.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 8.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 9.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme | |
Multi-step reaction with 9 steps 2: trifluoroacetic acid; polytetrafluoroethylene 3: acetic anhydride; pyridine; dmap 4: tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride 6: zinc 7: C6H6NO(1+)*C7H7O3S(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene; oxalic acid / dichloromethane; N,N-dimethyl-formamide / 20 °C 9: silver nitrate / acetonitrile; water / 20 °C View Scheme |
(1R,9S,10R,12R)-11-[(R)-2-Acetoxy-1-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-3-allyloxy-10-cyano-12-formyl-4-methoxy-5-methyl-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-13-carboxylic acid allyl ester
ecteinascidin 743
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C 2.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C 3.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C 4.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 5.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 6.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 7.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 8.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 9.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 9.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 9.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 10.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 11.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme | |
Multi-step reaction with 11 steps 1: trifluoroacetic acid / dichloromethane 2: potassium carbonate / methanol 4: trifluoroacetic acid; polytetrafluoroethylene 5: acetic anhydride; pyridine; dmap 6: tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride 8: zinc 9: C6H6NO(1+)*C7H7O3S(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene; oxalic acid / dichloromethane; N,N-dimethyl-formamide / 20 °C 11: silver nitrate / acetonitrile; water / 20 °C View Scheme |
(1R,9S,10R,12R)-11-[(R)-2-Acetoxy-1-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-3-allyloxy-10-cyano-12-hydroxymethyl-4-methoxy-5-methyl-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-13-carboxylic acid allyl ester
ecteinascidin 743
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C 2.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C 3.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C 4.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C 5.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 6.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 7.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 8.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 9.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 10.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 10.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 10.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 11.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 12.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme | |
Multi-step reaction with 12 steps 1: Dess-Martin periodane / dichloromethane 2: trifluoroacetic acid / dichloromethane 3: potassium carbonate / methanol 5: trifluoroacetic acid; polytetrafluoroethylene 6: acetic anhydride; pyridine; dmap 7: tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride 9: zinc 10: C6H6NO(1+)*C7H7O3S(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene; oxalic acid / dichloromethane; N,N-dimethyl-formamide / 20 °C 12: silver nitrate / acetonitrile; water / 20 °C View Scheme |
C34H37N3O10
ecteinascidin 743
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C 2.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C 3.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 4.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 5.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 6.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 7.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 8.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 8.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 8.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 9.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 10.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme | |
Multi-step reaction with 10 steps 1: potassium carbonate / methanol 3: trifluoroacetic acid; polytetrafluoroethylene 4: acetic anhydride; pyridine; dmap 5: tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride 7: zinc 8: C6H6NO(1+)*C7H7O3S(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene; oxalic acid / dichloromethane; N,N-dimethyl-formamide / 20 °C 10: silver nitrate / acetonitrile; water / 20 °C View Scheme |
(1R,3S)-3-Acetoxymethyl-8-allyloxy-1-((R)-1-{[(R)-ethoxycarbonyl-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-methyl]-amino}-2-hydroxy-ethyl)-7-methoxy-6-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid allyl ester
ecteinascidin 743
Conditions | Yield |
---|---|
Multi-step reaction with 19 steps 1.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C 2.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C 3.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C 4.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C 5.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C 6.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 7.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C 8.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C 9.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C 10.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C 11.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C 12.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 13.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 14.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 15.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 16.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 17.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 17.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 17.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 18.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 19.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme |
ecteinascidin 743
Conditions | Yield |
---|---|
Multi-step reaction with 16 steps 1.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C 2.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C 3.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 4.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C 5.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C 6.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C 7.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C 8.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C 9.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 10.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 11.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 12.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 13.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 14.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 14.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 14.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 15.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 16.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme |
3-allyloxy-12-(tert-butyl-dimethyl-silanyloxymethyl)-10-cyano-11-[2-hydroxy-1-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-4-methoxy-5-methyl-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-13-carboxylic acid allyl ester
ecteinascidin 743
Conditions | Yield |
---|---|
Multi-step reaction with 14 steps 1.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 2.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C 3.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C 4.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C 5.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C 6.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C 7.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 8.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 9.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 10.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 11.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 12.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 12.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 12.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 13.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 14.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme | |
Multi-step reaction with 13 steps 1: pyridine; dmap 2: Dess-Martin periodane / dichloromethane 3: trifluoroacetic acid / dichloromethane 4: potassium carbonate / methanol 6: trifluoroacetic acid; polytetrafluoroethylene 7: acetic anhydride; pyridine; dmap 8: tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride 10: zinc 11: C6H6NO(1+)*C7H7O3S(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene; oxalic acid / dichloromethane; N,N-dimethyl-formamide / 20 °C 13: silver nitrate / acetonitrile; water / 20 °C View Scheme |
(1R,3S)-8-Allyloxy-1-((R)-2-(tert-butyl-dimethyl-silanyloxy)-1-{[(R)-ethoxycarbonyl-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-methyl]-amino}-ethyl)-3-hydroxymethyl-7-methoxy-6-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid allyl ester
ecteinascidin 743
Conditions | Yield |
---|---|
Multi-step reaction with 17 steps 1.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C 2.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C 3.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C 4.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 5.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C 6.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C 7.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C 8.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C 9.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C 10.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 11.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 12.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 13.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 14.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 15.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 15.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 15.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 16.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 17.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme |
C34H35Cl3N4O10S
ecteinascidin 743
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 2.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 2.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 2.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 3.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 4.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme | |
Multi-step reaction with 4 steps 1: zinc 2: C6H6NO(1+)*C7H7O3S(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene; oxalic acid / dichloromethane; N,N-dimethyl-formamide / 20 °C 4: silver nitrate / acetonitrile; water / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 0 - 5 °C 2.1: zinc / tetrahydrofuran; methanol; aq. phosphate buffer / 25 - 30 °C 3.1: zinc(II) sulfate; magnesium glyoxylate / acetonitrile / 1 h / 20 - 25 °C 4.1: acetic acid / ethanol / 5 h / 20 - 25 °C 5.1: trifluoroacetic acid / tetrahydrofuran; water / 16 h / 20 - 25 °C 5.2: 18 h / 20 - 25 °C View Scheme |
3-allyloxy-12-(tert-butyl-dimethyl-silanyloxymethyl)-10-cyano-11-[ethoxycarbonyl-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-methyl]-4-methoxy-5-methyl-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-13-carboxylic acid allyl ester
ecteinascidin 743
Conditions | Yield |
---|---|
Multi-step reaction with 15 steps 1.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C 2.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 3.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C 4.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C 5.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C 6.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C 7.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C 8.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 9.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 10.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 11.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 12.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 13.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 13.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 13.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 14.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 15.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme | |
Multi-step reaction with 14 steps 1: lithium borohydride / methanol; tetrahydrofuran / 10 h / 0 °C 2: pyridine; dmap 3: Dess-Martin periodane / dichloromethane 4: trifluoroacetic acid / dichloromethane 5: potassium carbonate / methanol 7: trifluoroacetic acid; polytetrafluoroethylene 8: acetic anhydride; pyridine; dmap 9: tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride 11: zinc 12: C6H6NO(1+)*C7H7O3S(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene; oxalic acid / dichloromethane; N,N-dimethyl-formamide / 20 °C 14: silver nitrate / acetonitrile; water / 20 °C View Scheme |
11-[2-acetoxy-1-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-3-allyloxy-12-(tert-butyl-dimethyl-silanyloxymethyl)-10-cyano-4-methoxy-5-methyl-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-13-carboxylic acid allyl ester
ecteinascidin 743
Conditions | Yield |
---|---|
Multi-step reaction with 13 steps 1.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C 2.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C 3.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C 4.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C 5.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C 6.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 7.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 8.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 9.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 10.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 11.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 11.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 11.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 12.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 13.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme | |
Multi-step reaction with 13 steps 1: hydrogen fluoride / water 2: Dess-Martin periodane / dichloromethane 3: trifluoroacetic acid / dichloromethane 4: potassium carbonate / methanol 6: trifluoroacetic acid; polytetrafluoroethylene 7: acetic anhydride; pyridine; dmap 8: tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride 10: zinc 11: C6H6NO(1+)*C7H7O3S(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene; oxalic acid / dichloromethane; N,N-dimethyl-formamide / 20 °C 13: silver nitrate / acetonitrile; water / 20 °C View Scheme |
(1R,3S)-3-Acetoxymethyl-8-allyloxy-1-((R)-2-(tert-butyl-dimethyl-silanyloxy)-1-{[(R)-ethoxycarbonyl-(6-methoxymethoxy-7-methyl-benzo[1,3]dioxol-4-yl)-methyl]-amino}-ethyl)-7-methoxy-6-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid allyl ester
ecteinascidin 743
Conditions | Yield |
---|---|
Multi-step reaction with 18 steps 1.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C 2.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C 3.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C 4.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C 5.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 6.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C 7.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C 8.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C 9.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C 10.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C 11.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 12.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 13.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 14.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 15.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 16.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 16.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 16.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 17.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 18.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme |
C33H33Cl3N4O10S
ecteinascidin 743
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 2.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 3.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 3.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 3.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 4.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 5.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme | |
Multi-step reaction with 5 steps 2: zinc 3: C6H6NO(1+)*C7H7O3S(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene; oxalic acid / dichloromethane; N,N-dimethyl-formamide / 20 °C 5: silver nitrate / acetonitrile; water / 20 °C View Scheme |
C38H39Cl3N4O11S
ecteinascidin 743
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 2.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 3.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 4.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 5.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 5.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 5.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 6.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 7.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme | |
Multi-step reaction with 7 steps 1: acetic anhydride; pyridine; dmap 2: tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride 4: zinc 5: C6H6NO(1+)*C7H7O3S(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene; oxalic acid / dichloromethane; N,N-dimethyl-formamide / 20 °C 7: silver nitrate / acetonitrile; water / 20 °C View Scheme |
C40H41Cl3N4O12S
ecteinascidin 743
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 2.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 3.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 4.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 4.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 4.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 5.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 6.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme | |
Multi-step reaction with 6 steps 1: tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride 3: zinc 4: C6H6NO(1+)*C7H7O3S(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene; oxalic acid / dichloromethane; N,N-dimethyl-formamide / 20 °C 6: silver nitrate / acetonitrile; water / 20 °C View Scheme |
C60H61Cl3N4O15S
ecteinascidin 743
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 2.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 3.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 4.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 5.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 6.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 6.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 6.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 7.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 8.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme |
Sesamol
ecteinascidin 743
Conditions | Yield |
---|---|
Multi-step reaction with 26 steps 1.1: 96 percent / NaH / diethyl ether; dimethylformamide / 0 - 20 °C 2.1: n-BuLi; B(OMe)3 / tetrahydrofuran 2.2: 95 percent / AcOH; H2O2 / 0 - 20 °C 3.1: 97 percent / LiCl; 3 Angstroem molecular sieves / toluene; various solvent(s) / 24 h / 20 °C 4.1: 95 percent / K2CO3 / dimethylformamide / 1 h / 23 °C 5.1: 93 percent / K3PO4; Pd(PPh3)4 / dioxane / 4 h / 100 °C 6.1: 91 percent / benzotriazole; thionyl bromide / CH2Cl2 / 0.33 h / 20 °C 7.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C 8.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C 9.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C 10.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C 11.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C 12.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C 13.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 14.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C 15.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C 16.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C 17.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C 18.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C 19.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 20.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 21.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 22.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 23.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 24.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 24.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 24.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 25.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 26.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme | |
Multi-step reaction with 47 steps 1.1: NaH / tetrahydrofuran; dimethylformamide; various solvent(s) / 0 - 20 °C 1.2: 97 percent / tetrahydrofuran; dimethylformamide; various solvent(s) / 0 - 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 0 - 20 °C 2.2: 92 percent / aq. H2O2; trimethylboronate; AcOH / tetrahydrofuran; hexane / 4.5 h / 20 °C 3.1: 89 percent / TFA / CH2Cl2 / 2.17 h / -10 °C 4.1: 90 percent / pyridine / CH2Cl2 / 0.08 h / 0 °C 5.1: 85 percent / NaBH4 / methanol / 0.5 h / 0 °C 6.1: 91 percent / imidazole / dimethylformamide / 20 °C 7.1: 97 percent / PdCl2(dppf) / tetrahydrofuran / 4.5 h / Heating 8.1: Pb(OAc)4 / acetonitrile / 0 °C 9.1: 436 mg / NH2OH*HCl; NaOAc / ethanol / 1.5 h / 20 °C 10.1: 90 percent / methanol / 1 h / Heating 11.1: 89 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C 12.1: 93 percent / pyridine; DMAP / 30 h / 50 °C 13.1: TFA; anisole / CH2Cl2 / 9 h / 20 °C 14.1: 19.7 g / ethyl acetate / 1 h / Heating 15.1: 91 percent / TEA / CH2Cl2 / 1 h / 0 °C 16.1: 97 percent / DMAP / acetonitrile / 6.5 h / 20 °C 17.1: NaBH4; H2SO4 / ethanol; CH2Cl2 / 0 °C 18.1: 3.54 g / CSA; quinoline / toluene / 3 h / Heating 19.1: 83 percent / tris(dibenzylideneacetone)dipalladium(0); tris(o-tolyl)phosphine; TEA / acetonitrile / 2 h / Heating 20.1: aq. NaOH / methanol / 2.5 h / Heating 21.1: 106 mg / pyridine; DMAP / CH2Cl2 / 20 °C 22.1: TFA / CH2Cl2 / 4 h / 20 °C 23.1: 2.08 g / NaHCO3 / CH2Cl2; H2O / 0.17 h / 0 °C 24.1: dimethyldioxirane / methanol; acetone / 2 h / 0 °C 25.1: 652 mg / CSA / acetone / 0 - 20 °C 26.1: 94 percent / sodium cyanoborohydride; TFA / tetrahydrofuran / 0.5 h / 0 °C 27.1: 92 percent / imidazole / dimethylformamide / 2 h / 20 °C 28.1: 85 percent / guanidinium nitrate; NaOMe / methanol; CH2Cl2 / 2.5 h / 40 °C 29.1: 91 percent / K2CO3 / acetonitrile / 1 h / Heating 30.1: 82 percent / Red-Al / tetrahydrofuran; toluene / 0 °C 31.1: 73 percent / BF3*OEt2 / CH2Cl2 / 0 °C 32.1: 92 percent / pyridine; DMAP / 20 °C 33.1: 100 percent / aq. HF / acetonitrile / 3 h / 20 °C 34.1: 92 percent / Dess-Martin periodinane / CH2Cl2 / 0.67 h / 20 °C 35.1: 84 percent / H2 / Pd/C / tetrahydrofuran / 18 h / 20 °C / 760.05 Torr 36.1: 89 percent / i-Pr2NEt / CH2Cl2 / 3 h / Heating 37.1: 99 percent / K2CO3 / methanol / 0.5 h / 20 °C 38.1: 94 percent / WSCD*HCl; DMAP / CH2Cl2 / 0.17 h / 20 °C 39.1: 98 percent / hydrazine / acetonitrile / 1.33 h / 20 °C 40.1: TFA / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 41.1: 18.0 mg / pyridine; DMAP / 0.5 h / 20 °C 42.1: 92 percent / Zn; AcOH / diethyl ether / 2.5 h / 20 °C 43.1: 96 percent / AcOH; sodium cyanoborohydride / methanol / 1 h / 20 °C 44.1: 89 percent / Pd(PPh3)2Cl2; AcOH; n-Bu3SnH / CH2Cl2 / 0.33 h / 20 °C 45.1: 4-formyl-1-methylpyridinium benzenesulfonate / dimethylformamide; CH2Cl2 / 0.25 h / 20 °C 45.2: DBU / dimethylformamide; CH2Cl2 / 0.42 h / 20 °C 45.3: 54 percent / aq. citric acid / CH2Cl2; dimethylformamide / 0.67 h / 20 °C 46.1: 96 percent / sodium acetate / ethanol / 5.5 h / 20 °C 47.1: 93 percent / silver nitrate / acetoni View Scheme |
(3,4-methylenedioxyphenoxy)methyl methyl ether
ecteinascidin 743
Conditions | Yield |
---|---|
Multi-step reaction with 25 steps 1.1: n-BuLi; B(OMe)3 / tetrahydrofuran 1.2: 95 percent / AcOH; H2O2 / 0 - 20 °C 2.1: 97 percent / LiCl; 3 Angstroem molecular sieves / toluene; various solvent(s) / 24 h / 20 °C 3.1: 95 percent / K2CO3 / dimethylformamide / 1 h / 23 °C 4.1: 93 percent / K3PO4; Pd(PPh3)4 / dioxane / 4 h / 100 °C 5.1: 91 percent / benzotriazole; thionyl bromide / CH2Cl2 / 0.33 h / 20 °C 6.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C 7.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C 8.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C 9.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C 10.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C 11.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C 12.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 13.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C 14.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C 15.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C 16.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C 17.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C 18.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 19.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 20.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 21.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 22.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 23.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 23.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 23.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 24.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 25.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme | |
Multi-step reaction with 46 steps 1.1: n-BuLi / tetrahydrofuran; hexane / 0 - 20 °C 1.2: 92 percent / aq. H2O2; trimethylboronate; AcOH / tetrahydrofuran; hexane / 4.5 h / 20 °C 2.1: 89 percent / TFA / CH2Cl2 / 2.17 h / -10 °C 3.1: 90 percent / pyridine / CH2Cl2 / 0.08 h / 0 °C 4.1: 85 percent / NaBH4 / methanol / 0.5 h / 0 °C 5.1: 91 percent / imidazole / dimethylformamide / 20 °C 6.1: 97 percent / PdCl2(dppf) / tetrahydrofuran / 4.5 h / Heating 7.1: Pb(OAc)4 / acetonitrile / 0 °C 8.1: 436 mg / NH2OH*HCl; NaOAc / ethanol / 1.5 h / 20 °C 9.1: 90 percent / methanol / 1 h / Heating 10.1: 89 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C 11.1: 93 percent / pyridine; DMAP / 30 h / 50 °C 12.1: TFA; anisole / CH2Cl2 / 9 h / 20 °C 13.1: 19.7 g / ethyl acetate / 1 h / Heating 14.1: 91 percent / TEA / CH2Cl2 / 1 h / 0 °C 15.1: 97 percent / DMAP / acetonitrile / 6.5 h / 20 °C 16.1: NaBH4; H2SO4 / ethanol; CH2Cl2 / 0 °C 17.1: 3.54 g / CSA; quinoline / toluene / 3 h / Heating 18.1: 83 percent / tris(dibenzylideneacetone)dipalladium(0); tris(o-tolyl)phosphine; TEA / acetonitrile / 2 h / Heating 19.1: aq. NaOH / methanol / 2.5 h / Heating 20.1: 106 mg / pyridine; DMAP / CH2Cl2 / 20 °C 21.1: TFA / CH2Cl2 / 4 h / 20 °C 22.1: 2.08 g / NaHCO3 / CH2Cl2; H2O / 0.17 h / 0 °C 23.1: dimethyldioxirane / methanol; acetone / 2 h / 0 °C 24.1: 652 mg / CSA / acetone / 0 - 20 °C 25.1: 94 percent / sodium cyanoborohydride; TFA / tetrahydrofuran / 0.5 h / 0 °C 26.1: 92 percent / imidazole / dimethylformamide / 2 h / 20 °C 27.1: 85 percent / guanidinium nitrate; NaOMe / methanol; CH2Cl2 / 2.5 h / 40 °C 28.1: 91 percent / K2CO3 / acetonitrile / 1 h / Heating 29.1: 82 percent / Red-Al / tetrahydrofuran; toluene / 0 °C 30.1: 73 percent / BF3*OEt2 / CH2Cl2 / 0 °C 31.1: 92 percent / pyridine; DMAP / 20 °C 32.1: 100 percent / aq. HF / acetonitrile / 3 h / 20 °C 33.1: 92 percent / Dess-Martin periodinane / CH2Cl2 / 0.67 h / 20 °C 34.1: 84 percent / H2 / Pd/C / tetrahydrofuran / 18 h / 20 °C / 760.05 Torr 35.1: 89 percent / i-Pr2NEt / CH2Cl2 / 3 h / Heating 36.1: 99 percent / K2CO3 / methanol / 0.5 h / 20 °C 37.1: 94 percent / WSCD*HCl; DMAP / CH2Cl2 / 0.17 h / 20 °C 38.1: 98 percent / hydrazine / acetonitrile / 1.33 h / 20 °C 39.1: TFA / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 40.1: 18.0 mg / pyridine; DMAP / 0.5 h / 20 °C 41.1: 92 percent / Zn; AcOH / diethyl ether / 2.5 h / 20 °C 42.1: 96 percent / AcOH; sodium cyanoborohydride / methanol / 1 h / 20 °C 43.1: 89 percent / Pd(PPh3)2Cl2; AcOH; n-Bu3SnH / CH2Cl2 / 0.33 h / 20 °C 44.1: 4-formyl-1-methylpyridinium benzenesulfonate / dimethylformamide; CH2Cl2 / 0.25 h / 20 °C 44.2: DBU / dimethylformamide; CH2Cl2 / 0.42 h / 20 °C 44.3: 54 percent / aq. citric acid / CH2Cl2; dimethylformamide / 0.67 h / 20 °C 45.1: 96 percent / sodium acetate / ethanol / 5.5 h / 20 °C 46.1: 93 percent / silver nitrate / acetonitrile; H2O / 17 h / 20 °C View Scheme | |
Multi-step reaction with 33 steps 1: 1.) BuLi, tetramethylethylene diamine / 1.) hexane, 0 deg C, 4 h, 2.) hexane, from -78 deg C to 23 deg C, 15 min 2: 1.) BuLi / 1.) THF, -30 deg C, 13 h 3: CH3SO3H / CH2Cl2 / 0 °C 4: 1.) NaH / 1.) DMF, 0 deg C, 5 min, 2.) DMF, 23 deg C, 40 min 5: 99 percent / piperidine, acetic acid / benzene / 18 h / 23 °C 6: 94 percent / Et3N, HCOOH, Pd(PPh3)4 / 4 h / 23 °C 7: (PhO)2P(O)N3, Et3N, 4 Angstroem molecular sieves / toluene / 2 h / 70 °C 8: 1 h / 23 °C 9: 97 percent / H2, Rh<(COD)-(R,R)-DIPAMP>(+)*BF4(-) / 16 h / 23 °C / 2280 Torr 10: BF3*Et2O, H2O / CH2Cl2 / 0.17 h / 0 °C 11: BF3*Et2O, 4 Angstroem molecular sieves / CH2Cl2 / 18 h / 23 °C 12: 100 percent / H2 / 10percent Pd/C / ethyl acetate / 6 h / 23 °C / 760 Torr 13: 61 percent / HOAc / 18 h / 23 °C 14: 87 percent / Cs2CO3 / dimethylformamide / 1 h / 23 °C 15: diisobutylaluminum hydride / toluene / 5 h / -78 °C 16: KF*2H2O / methanol / 0.33 h / 23 °C 17: CH3SO3H, 3 Angstroem molecular sieves / CH2Cl2 / 5 h / 23 °C 18: 72 percent / Et3N, DMAP / CH2Cl2 / 6 h / 23 °C 19: 89 percent / DMAP / CH2Cl2 / 13 h / 23 °C 20: 92 percent / i-Pr2NEt / CH2Cl2 / 0.33 h / 23 °C 21: 1.) Bu3SnH, PdCl2(PPh3)2, HOAc, 2.) NaBH3CN, HOAc / 1.) CH2Cl2, 23 deg C, 15 min, 2.) CH3CN, 23 deg C, 30 min 22: 83 percent / PdCl2(PPh3)2, LiCl / dimethylformamide / 2 h / 80 °C 23: (PhSeO)2O / CH2Cl2 / 0.25 h / 23 °C 24: Bu4NF / tetrahydrofuran / 0.17 h / 23 °C 25: 91 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, DMAP / CH2Cl2 / 0.5 h / 23 °C 26: 0.5 h / -40 °C 27: 1.) i-Pr2NEt, 2.) tert-butyl alcohol, N-tert-butyl-N',N',N'',N''-tetramethylguanidine / 1.) 0 deg C, 30 min, 2.) 23 deg C 28: 23 °C 29: 84 percent / PdCl2(PPh3)2, Bu3SnH, HOAc / CH2Cl2 / 0.08 h / 23 °C 30: 70 percent / iodide, 1,8-diazabicyclo<6.4.0>undec-7-ene, DMF / CH2Cl2 / 0.67 h / 23 °C 31: 82 percent / silica gel / ethanol / 23 °C 32: aq. CF3COOH / tetrahydrofuran / 9 h / 23 °C 33: aq. AgNO3 / acetonitrile / 11 h / 23 °C View Scheme |
4-hydroxy-5-(methoxymethoxy)-1,3-benzodioxole
ecteinascidin 743
Conditions | Yield |
---|---|
Multi-step reaction with 24 steps 1.1: 97 percent / LiCl; 3 Angstroem molecular sieves / toluene; various solvent(s) / 24 h / 20 °C 2.1: 95 percent / K2CO3 / dimethylformamide / 1 h / 23 °C 3.1: 93 percent / K3PO4; Pd(PPh3)4 / dioxane / 4 h / 100 °C 4.1: 91 percent / benzotriazole; thionyl bromide / CH2Cl2 / 0.33 h / 20 °C 5.1: 68 percent / triethylamine / acetonitrile / 14 h / 0 °C 6.1: 97 percent / imidazole / dimethylformamide / 3 h / 23 °C 7.1: 94 percent / K2CO3; MeOH / 2 h / 23 °C 8.1: Dess-Martin periodinane / CH2Cl2 / 0.33 h / 23 °C 9.1: 1.26 g / ZnCl2 / CH2Cl2; tetrahydrofuran / 0.17 h / 23 °C 10.1: 80 percent / LiBH4 / tetrahydrofuran; methanol / 10 h / 0 °C 11.1: 92 percent / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 12.1: 91 percent / aq. HF / acetonitrile / 2 h / 23 °C 13.1: 93 percent / Dess-Martin periodinane / CH2Cl2 / 0.33 h / 20 °C 14.1: 95 percent / CF3COOH / CH2Cl2 / 0.5 h / 23 °C 15.1: 96 percent / K2CO3; MeOH / 1 h / 20 °C 16.1: 95 percent / DMAP; EDCl / CH2Cl2 / 1 h / 20 °C 17.1: CF3COOH / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 18.1: 143 mg / pyridine; DMAP / CH2Cl2 / 0.5 h / 23 °C 19.1: 87 percent / n-Bu3SnH; AcOH; Pd(PPh3)2Cl2 / CH2Cl2 / 0.33 h / 20 °C 20.1: 97 percent / NaBH3CN; AcOH / acetonitrile; methanol / 2 h / 23 °C 21.1: 92 percent / Zn; AcOH / diethyl ether / 1 h / 23 °C 22.1: 4-formyl-1-methylpyridinium benzenesulfonate / CH2Cl2; dimethylformamide / 0.17 h / 23 °C 22.2: DBU / CH2Cl2; dimethylformamide / 0.25 h / 23 °C 22.3: 53 percent / aq. oxalic acid / CH2Cl2; dimethylformamide / 0.5 h / 23 °C 23.1: 97 percent / NaOAc / ethanol / 3 h / 23 °C 24.1: 92 percent / aq. AgNO3 / acetonitrile / 19 h / 23 °C View Scheme | |
Multi-step reaction with 45 steps 1.1: 89 percent / TFA / CH2Cl2 / 2.17 h / -10 °C 2.1: 90 percent / pyridine / CH2Cl2 / 0.08 h / 0 °C 3.1: 85 percent / NaBH4 / methanol / 0.5 h / 0 °C 4.1: 91 percent / imidazole / dimethylformamide / 20 °C 5.1: 97 percent / PdCl2(dppf) / tetrahydrofuran / 4.5 h / Heating 6.1: Pb(OAc)4 / acetonitrile / 0 °C 7.1: 436 mg / NH2OH*HCl; NaOAc / ethanol / 1.5 h / 20 °C 8.1: 90 percent / methanol / 1 h / Heating 9.1: 89 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C 10.1: 93 percent / pyridine; DMAP / 30 h / 50 °C 11.1: TFA; anisole / CH2Cl2 / 9 h / 20 °C 12.1: 19.7 g / ethyl acetate / 1 h / Heating 13.1: 91 percent / TEA / CH2Cl2 / 1 h / 0 °C 14.1: 97 percent / DMAP / acetonitrile / 6.5 h / 20 °C 15.1: NaBH4; H2SO4 / ethanol; CH2Cl2 / 0 °C 16.1: 3.54 g / CSA; quinoline / toluene / 3 h / Heating 17.1: 83 percent / tris(dibenzylideneacetone)dipalladium(0); tris(o-tolyl)phosphine; TEA / acetonitrile / 2 h / Heating 18.1: aq. NaOH / methanol / 2.5 h / Heating 19.1: 106 mg / pyridine; DMAP / CH2Cl2 / 20 °C 20.1: TFA / CH2Cl2 / 4 h / 20 °C 21.1: 2.08 g / NaHCO3 / CH2Cl2; H2O / 0.17 h / 0 °C 22.1: dimethyldioxirane / methanol; acetone / 2 h / 0 °C 23.1: 652 mg / CSA / acetone / 0 - 20 °C 24.1: 94 percent / sodium cyanoborohydride; TFA / tetrahydrofuran / 0.5 h / 0 °C 25.1: 92 percent / imidazole / dimethylformamide / 2 h / 20 °C 26.1: 85 percent / guanidinium nitrate; NaOMe / methanol; CH2Cl2 / 2.5 h / 40 °C 27.1: 91 percent / K2CO3 / acetonitrile / 1 h / Heating 28.1: 82 percent / Red-Al / tetrahydrofuran; toluene / 0 °C 29.1: 73 percent / BF3*OEt2 / CH2Cl2 / 0 °C 30.1: 92 percent / pyridine; DMAP / 20 °C 31.1: 100 percent / aq. HF / acetonitrile / 3 h / 20 °C 32.1: 92 percent / Dess-Martin periodinane / CH2Cl2 / 0.67 h / 20 °C 33.1: 84 percent / H2 / Pd/C / tetrahydrofuran / 18 h / 20 °C / 760.05 Torr 34.1: 89 percent / i-Pr2NEt / CH2Cl2 / 3 h / Heating 35.1: 99 percent / K2CO3 / methanol / 0.5 h / 20 °C 36.1: 94 percent / WSCD*HCl; DMAP / CH2Cl2 / 0.17 h / 20 °C 37.1: 98 percent / hydrazine / acetonitrile / 1.33 h / 20 °C 38.1: TFA / 2,2,2-trifluoro-ethanol / 3 h / 20 °C 39.1: 18.0 mg / pyridine; DMAP / 0.5 h / 20 °C 40.1: 92 percent / Zn; AcOH / diethyl ether / 2.5 h / 20 °C 41.1: 96 percent / AcOH; sodium cyanoborohydride / methanol / 1 h / 20 °C 42.1: 89 percent / Pd(PPh3)2Cl2; AcOH; n-Bu3SnH / CH2Cl2 / 0.33 h / 20 °C 43.1: 4-formyl-1-methylpyridinium benzenesulfonate / dimethylformamide; CH2Cl2 / 0.25 h / 20 °C 43.2: DBU / dimethylformamide; CH2Cl2 / 0.42 h / 20 °C 43.3: 54 percent / aq. citric acid / CH2Cl2; dimethylformamide / 0.67 h / 20 °C 44.1: 96 percent / sodium acetate / ethanol / 5.5 h / 20 °C 45.1: 93 percent / silver nitrate / acetonitrile; H2O / 17 h / 20 °C View Scheme |
ecteinascidin 743
Conditions | Yield |
---|---|
With sodium cyanoborohydride; acetic acid In acetonitrile at 23℃; for 0.5h; | 64% |
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