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Pribolab PTE.LTD

This series products include: 500 µg/mL Bongkrekic Acid in Tris buffer (0.1M,pH7.5) 100 µg/mL Bongkrekic Acid in Methanol 1000 µg/mL Bongkrekic Acid in Acetonitrile (0.1%,Ammonia) Appearance:bottle Storage:-20℃ Application:Determ

Bongkrekic Acid in Tris buffer

Cas:11076-19-0

Min.Order:0 Metric Ton

Negotiable

Type:Trading Company

inquiry

Hebei Nengqian Chemical Import and Export Co., LTD

With our good experience, we offer detailed technical support and advice to assist customers. We communicate closely with customers to establish their quality requirements. Consistent Quality Our plant has strict quality control in each manufacturin

BONGKREKIC ACID

Cas:11076-19-0

Min.Order:1 Kilogram

FOB Price: $1.0 / 10.0

Type:Trading Company

inquiry

Zhuozhou 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

Pharmaceutical Grade CAS 11076-19-0 with competitive price

Cas:11076-19-0

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

inquiry

Hebei Sankai Chemical Technology Co., Ltd

1. Product advantages High purity, all above 98.5%, no impurities after dissolution We will test each batch to ensure quality OEM and private brand services designed for free Various cap colors available We can also provide MT1 peptide powd

Bongkrekic acidCAS11076-19-0

Cas:11076-19-0

Min.Order:1 Kilogram

FOB Price: $10.0 / 20.0

Type:Trading Company

inquiry

Shanghai Upbio Tech Co.,Ltd

1.No Less 8 years exporting experience. Clients 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 Specialized

Qingdao Beluga Import and Export Co., LTD

BONGKREKIC ACID CAS:11076-19-0 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 intermedi

BONGKREKIC ACID CAS:11076-19-0

Cas:11076-19-0

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Shandong 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

Henan 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

Wuhan Han Sheng New Material Technology Co.,Ltd

Our advantage: high quality with competitive price High quality standard: BP/USP/EP Enterprise standard All purity customized Fast and safe delivery We have reliable forwarder who can help us deliver our goods more fast and safe. We have s

Bongkrekic acid solution

Cas:11076-19-0

Min.Order:10 Kilogram

Negotiable

Type:Trading Company

inquiry

Hangzhou J&H Chemical Co., Ltd.

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

Zibo 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

EAST CHEMSOURCES LIMITED

factory?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

Bongkrekic acid solution

Cas:11076-19-0

Min.Order:1 Kilogram

FOB Price: $18.0 / 20.0

Type:Trading Company

inquiry

Hangzhou Huarong Pharm Co., Ltd.

Hangzhou Huarong Pharm Co., Ltd.established since 2006 , has been actively developing specialty products for Finished Dosages, APIs, Intermediates, and Fine chemicals markets in North America, Europe, Korea, Japan, Mid-East and all over the World. Hu

Bongkrekic Acid

Cas:11076-19-0

Min.Order:0

Negotiable

Type:Trading Company

inquiry

Shandong Mopai Biotechnology Co., LTD

Shandong 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

Bongkrekic acid solution

Cas:11076-19-0

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

KAISA GROUP INC

1.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

Bongkrekic acid solution

Cas:11076-19-0

Min.Order:1 Metric Ton

FOB Price: $1.5

Type:Trading Company

inquiry

Bluecrystal chem-union

We are a Union of chemistry in China, consists of chemists,engineers, laboratories,factories in China. We organize surplus capacity of R&D and production as well as custom synthesis for chemical products and chemical business project. We are supp

Bongkrekic acid solution

Cas:11076-19-0

Min.Order:1 Metric Ton

FOB Price: $1.0

Type:Trading Company

inquiry

Hangzhou Dingyan Chem Co., Ltd

R & D enterprises have their own stock in stock Package:1kg Application:pharmaceutical intermediates

Henan 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

BONGKREKIC ACID

Cas:11076-19-0

Min.Order:0

Negotiable

Type:Manufacturers

inquiry

Xi`an Eastling Biotech Co., Ltd.

high purity lowest priceAppearance:solid or liquid Storage:in sealed air resistant place Package:Foil bag; Drum; Plastic bottle Application:Pharma;Industry;Agricultural Transportation:by sea or air Port:Beijing or Guangzhou

BONGKREKIC ACID

Cas:11076-19-0

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Henan Tianfu Chemical Co., Ltd.

1.Our services:A.Supply sampleB.The packing also can be according the customers` requirmentC.Any inquiries will be replied within 24 hoursD.we provide Commerical Invoice, Packing List, Bill of loading, COA , Health certificate and Origin certificate.

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

Hubei Langyou International Trading Co., Ltd

Bongkrekic acid solution Application:Bongkrekic acid solution

Bongkrekic acid solution

Cas:11076-19-0

Min.Order:0

Negotiable

Type:Other

inquiry

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

BONGKREKIC ACID

Cas:11076-19-0

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Hunan Longxianng Runhui Trading Co.,Ltd

Bongkrekic acid solutionAppearance:ask Storage:keep in dry and cool condition Package:foil aluminium bag/vacuum packing Application:intermediates Transportation:By express (Door to door) such as FEDEX, DHL, EMS for small amount. By air(airport to air

Bongkrekic acid solution

Cas:11076-19-0

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Shanghai Chinqesen Biotechnology Co., Ltd.

Good Quality Package:1kg/bag Application:Medical or chemical Transportation:Air/Train/Sea Port:Shenzhen

11076-19-0

Cas:11076-19-0

Min.Order:0

Negotiable

Type:Trading Company

inquiry

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

BONGKREKIC ACID

Cas:11076-19-0

Min.Order:0

Negotiable

Type:Trading Company

inquiry

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

bongkrekic acid

Cas:11076-19-0

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

HuBei Ipure Biotech CO.,ltd

HuBei ipure is a diversified product production and operation enterprise, with API, pharma intermediates, and other fine chemicals as well as R&D and pigments development and sales as one of the large enterprises, with more than 130 acres of pl

Bongkrekic acid solution CAS NO.11076-19-0

Cas:11076-19-0

Min.Order:1 Gram

FOB Price: $1.0

Type:Trading Company

inquiry

Hubei Jusheng Technology Co., Ltd.,

1,Best Quality: Our products have exported to Germany, Spain, UK, USA, Australia, Middle East, and so on other countries, and we have got very good feedback from our customers.so you can trust us. 2,

Bongkrekic acid solution

Cas:11076-19-0

Min.Order:10 Gram

FOB Price: $1.0 / 2.0

Type:Trading Company

inquiry

Nanjing Raymon Biotech Co., Ltd.

2,4,8,10,14,18,20-Docosaheptaenedioicacid, 20-(carboxymethyl)-6-methoxy-2,5,17-trimethyl-,(2E,4Z,6R,8Z,10E,14E,17S,18E,20Z)- Storage:keep in dry and cool condition Package:25kg or according to cutomer's demand Application:Chemical research/pharma int

Synthetic route

(6R,17S)-bis(methoxymethyl) 20-(2-hydroxyethyl)-6-methoxy-2,5,17-trimethyldocosa-2,4,8,10,14,18,20-heptaenedioate

(6R,17S)-bis(methoxymethyl) 20-(2-hydroxyethyl)-6-methoxy-2,5,17-trimethyldocosa-2,4,8,10,14,18,20-heptaenedioate

bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
With hydrogenchloride; water In tetrahydrofuran at 0 - 20℃; for 1h;92%
(Z)-3-[(1E,3S,5E,9E,11Z,14R,15Z,17E)-19-tert-butoxy-14-methoxy-3,15,18-trimethyl-19-oxononadeca-1,5,9,11,15,17-hexaenyl]pent-2-enedioic acid
1196458-46-4

(Z)-3-[(1E,3S,5E,9E,11Z,14R,15Z,17E)-19-tert-butoxy-14-methoxy-3,15,18-trimethyl-19-oxononadeca-1,5,9,11,15,17-hexaenyl]pent-2-enedioic acid

bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
With hydrogenchloride; water In tetrahydrofuran at 20℃; for 3h;83%
(2E,4Z,8Z,10E,14E)-(6R,17S)-17-(4-Carboxymethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-6-methoxy-2,5-dimethyl-octadeca-2,4,8,10,14-pentaenoic acid
88304-12-5, 88335-55-1

(2E,4Z,8Z,10E,14E)-(6R,17S)-17-(4-Carboxymethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-6-methoxy-2,5-dimethyl-octadeca-2,4,8,10,14-pentaenoic acid

bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
With potassium methanolate In tetrahydrofuran; methanol at 0℃; for 0.0833333h;65%
C31H44O7

C31H44O7

A

bongkrekic acid
11076-19-0

bongkrekic acid

B

isobongkrekic acid
60132-21-0

isobongkrekic acid

Conditions
ConditionsYield
Stage #1: C31H44O7 With water; potassium hydroxide In 1,2-dimethoxyethane at 20℃; for 8h;
Stage #2: With hydrogenchloride In 1,2-dimethoxyethane; water optical yield given as %de; Further stages;
A 17%
B 35%
BAMe3

BAMe3

A

bongkrekic acid
11076-19-0

bongkrekic acid

B

isobongkrekic acid
60132-21-0

isobongkrekic acid

Conditions
ConditionsYield
With potassium hydroxide In 1,2-dimethoxyethane; water at 20℃; for 8h;A 35%
B 17%
(2E,4Z,8Z,10E,14E,18E,20Z)-(6R,17S)-20-Carboxymethyl-6-methoxy-2,5,17-trimethyl-docosa-2,4,8,10,14,18,20-heptaenedioic acid 1-tert-butyl ester 22-(tert-butyl-diphenyl-silanyloxymethyl) ester
808771-36-0

(2E,4Z,8Z,10E,14E,18E,20Z)-(6R,17S)-20-Carboxymethyl-6-methoxy-2,5,17-trimethyl-docosa-2,4,8,10,14,18,20-heptaenedioic acid 1-tert-butyl ester 22-(tert-butyl-diphenyl-silanyloxymethyl) ester

bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 20℃;
(Z)-4-((R)-3-Methyl-5-oxo-2,5-dihydro-furan-2-yl)-but-2-enal

(Z)-4-((R)-3-Methyl-5-oxo-2,5-dihydro-furan-2-yl)-but-2-enal

bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: 86 percent / BuLi; HMPA / tetrahydrofuran
2.1: DIBAH / tetrahydrofuran
2.2: 70 percent / NaBH4 / tetrahydrofuran; H2O
3.1: Dess-Martin reagent / benzene; CH2Cl2
4.1: 80 percent / benzene
5.1: 82 percent / HCl / H2O; tetrahydrofuran
6.1: MnO2 / benzene; CH2Cl2
6.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
6.3: 40 percent / Et3N / tetrahydrofuran
7.1: Dess-Martin reagent / benzene; CH2Cl2
7.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
8.1: HCl / H2O; methanol / 20 °C
View Scheme
Multi-step reaction with 14 steps
1.1: 86 percent / BuLi; HMPA / tetrahydrofuran
2.1: DIBAH / tetrahydrofuran
2.2: 70 percent / NaBH4 / tetrahydrofuran; H2O
3.1: 93 percent / Na-Hg; Na2HPO4 / methanol
4.1: 96 percent / Et3N / CH2Cl2
5.1: 83 percent / 2,6-di-tert-butylpyridine / benzene
6.1: 81 percent / DIBAH / tetrahydrofuran
7.1: Dess-Martin reagent / benzene; CH2Cl2
8.1: 80 percent / benzene
9.1: 82 percent / HCl / H2O; tetrahydrofuran
10.1: MnO2 / benzene; CH2Cl2
10.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
10.3: 40 percent / Et3N / tetrahydrofuran
11.1: Dess-Martin reagent / benzene; CH2Cl2
11.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
12.1: HCl / H2O; methanol / 20 °C
View Scheme
(R)-5-((Z)-4-Hydroxy-but-2-enyl)-4-methyl-5H-furan-2-one
808771-43-9

(R)-5-((Z)-4-Hydroxy-but-2-enyl)-4-methyl-5H-furan-2-one

bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: MnO2 / CH2Cl2
2.1: 86 percent / BuLi; HMPA / tetrahydrofuran
3.1: DIBAH / tetrahydrofuran
3.2: 70 percent / NaBH4 / tetrahydrofuran; H2O
4.1: Dess-Martin reagent / benzene; CH2Cl2
5.1: 80 percent / benzene
6.1: 82 percent / HCl / H2O; tetrahydrofuran
7.1: MnO2 / benzene; CH2Cl2
7.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
7.3: 40 percent / Et3N / tetrahydrofuran
8.1: Dess-Martin reagent / benzene; CH2Cl2
8.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
9.1: HCl / H2O; methanol / 20 °C
View Scheme
Multi-step reaction with 15 steps
1.1: MnO2 / CH2Cl2
2.1: 86 percent / BuLi; HMPA / tetrahydrofuran
3.1: DIBAH / tetrahydrofuran
3.2: 70 percent / NaBH4 / tetrahydrofuran; H2O
4.1: 93 percent / Na-Hg; Na2HPO4 / methanol
5.1: 96 percent / Et3N / CH2Cl2
6.1: 83 percent / 2,6-di-tert-butylpyridine / benzene
7.1: 81 percent / DIBAH / tetrahydrofuran
8.1: Dess-Martin reagent / benzene; CH2Cl2
9.1: 80 percent / benzene
10.1: 82 percent / HCl / H2O; tetrahydrofuran
11.1: MnO2 / benzene; CH2Cl2
11.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
11.3: 40 percent / Et3N / tetrahydrofuran
12.1: Dess-Martin reagent / benzene; CH2Cl2
12.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
13.1: HCl / H2O; methanol / 20 °C
View Scheme
(R)-5-((2Z,4E)-6-Bromo-hexa-2,4-dienyl)-4-methyl-5H-furan-2-one
808771-29-1

(R)-5-((2Z,4E)-6-Bromo-hexa-2,4-dienyl)-4-methyl-5H-furan-2-one

bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: 86 percent / BuLi; HMPA / tetrahydrofuran
2.1: DIBAH / tetrahydrofuran
2.2: 70 percent / NaBH4 / tetrahydrofuran; H2O
3.1: Dess-Martin reagent / benzene; CH2Cl2
4.1: 80 percent / benzene
5.1: 82 percent / HCl / H2O; tetrahydrofuran
6.1: MnO2 / benzene; CH2Cl2
6.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
6.3: 40 percent / Et3N / tetrahydrofuran
7.1: Dess-Martin reagent / benzene; CH2Cl2
7.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
8.1: HCl / H2O; methanol / 20 °C
View Scheme
Multi-step reaction with 12 steps
1.1: 86 percent / BuLi; HMPA / tetrahydrofuran
2.1: DIBAH / tetrahydrofuran
2.2: 70 percent / NaBH4 / tetrahydrofuran; H2O
3.1: 93 percent / Na-Hg; Na2HPO4 / methanol
4.1: 96 percent / Et3N / CH2Cl2
5.1: 83 percent / 2,6-di-tert-butylpyridine / benzene
6.1: 81 percent / DIBAH / tetrahydrofuran
7.1: Dess-Martin reagent / benzene; CH2Cl2
8.1: 80 percent / benzene
9.1: 82 percent / HCl / H2O; tetrahydrofuran
10.1: MnO2 / benzene; CH2Cl2
10.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
10.3: 40 percent / Et3N / tetrahydrofuran
11.1: Dess-Martin reagent / benzene; CH2Cl2
11.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
12.1: HCl / H2O; methanol / 20 °C
View Scheme
(2E,6E)-(S)-5-Methyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-hepta-2,6-dien-1-ol
808771-19-9

(2E,6E)-(S)-5-Methyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-hepta-2,6-dien-1-ol

bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: 92 percent / Et3N / PdCl2(PPh3)2 / methanol
2.1: MsCl; iPr2EtN; 4-DMAP / CH2Cl2
2.2: 81 percent / dimethylformamide
3.1: 86 percent / BuLi; HMPA / tetrahydrofuran
4.1: DIBAH / tetrahydrofuran
4.2: 70 percent / NaBH4 / tetrahydrofuran; H2O
5.1: Dess-Martin reagent / benzene; CH2Cl2
6.1: 80 percent / benzene
7.1: 82 percent / HCl / H2O; tetrahydrofuran
8.1: MnO2 / benzene; CH2Cl2
8.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
8.3: 40 percent / Et3N / tetrahydrofuran
9.1: Dess-Martin reagent / benzene; CH2Cl2
9.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
10.1: HCl / H2O; methanol / 20 °C
View Scheme
Multi-step reaction with 14 steps
1.1: 92 percent / Et3N / PdCl2(PPh3)2 / methanol
2.1: MsCl; iPr2EtN; 4-DMAP / CH2Cl2
2.2: 81 percent / dimethylformamide
3.1: 86 percent / BuLi; HMPA / tetrahydrofuran
4.1: DIBAH / tetrahydrofuran
4.2: 70 percent / NaBH4 / tetrahydrofuran; H2O
5.1: 93 percent / Na-Hg; Na2HPO4 / methanol
6.1: 96 percent / Et3N / CH2Cl2
7.1: 83 percent / 2,6-di-tert-butylpyridine / benzene
8.1: 81 percent / DIBAH / tetrahydrofuran
9.1: Dess-Martin reagent / benzene; CH2Cl2
10.1: 80 percent / benzene
11.1: 82 percent / HCl / H2O; tetrahydrofuran
12.1: MnO2 / benzene; CH2Cl2
12.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
12.3: 40 percent / Et3N / tetrahydrofuran
13.1: Dess-Martin reagent / benzene; CH2Cl2
13.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
14.1: HCl / H2O; methanol / 20 °C
View Scheme
(2E,4Z)-6-((R)-3-Methyl-5-oxo-2,5-dihydro-furan-2-yl)-hexa-2,4-dienoic acid tert-butyl ester
808771-28-0

(2E,4Z)-6-((R)-3-Methyl-5-oxo-2,5-dihydro-furan-2-yl)-hexa-2,4-dienoic acid tert-butyl ester

bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: 86 percent / BuLi; HMPA / tetrahydrofuran
2.1: DIBAH / tetrahydrofuran
2.2: 70 percent / NaBH4 / tetrahydrofuran; H2O
3.1: Dess-Martin reagent / benzene; CH2Cl2
4.1: 80 percent / benzene
5.1: 82 percent / HCl / H2O; tetrahydrofuran
6.1: MnO2 / benzene; CH2Cl2
6.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
6.3: 40 percent / Et3N / tetrahydrofuran
7.1: Dess-Martin reagent / benzene; CH2Cl2
7.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
8.1: HCl / H2O; methanol / 20 °C
View Scheme
Multi-step reaction with 13 steps
1.1: 86 percent / BuLi; HMPA / tetrahydrofuran
2.1: DIBAH / tetrahydrofuran
2.2: 70 percent / NaBH4 / tetrahydrofuran; H2O
3.1: 93 percent / Na-Hg; Na2HPO4 / methanol
4.1: 96 percent / Et3N / CH2Cl2
5.1: 83 percent / 2,6-di-tert-butylpyridine / benzene
6.1: 81 percent / DIBAH / tetrahydrofuran
7.1: Dess-Martin reagent / benzene; CH2Cl2
8.1: 80 percent / benzene
9.1: 82 percent / HCl / H2O; tetrahydrofuran
10.1: MnO2 / benzene; CH2Cl2
10.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
10.3: 40 percent / Et3N / tetrahydrofuran
11.1: Dess-Martin reagent / benzene; CH2Cl2
11.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
12.1: HCl / H2O; methanol / 20 °C
View Scheme
(R)-5-[(Z)-4-(4-Methoxy-benzyloxy)-but-2-enyl]-4-methyl-5H-furan-2-one
808771-27-9

(R)-5-[(Z)-4-(4-Methoxy-benzyloxy)-but-2-enyl]-4-methyl-5H-furan-2-one

bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: 92 percent / DDQ / CH2Cl2; H2O
2.1: MnO2 / CH2Cl2
3.1: 86 percent / BuLi; HMPA / tetrahydrofuran
4.1: DIBAH / tetrahydrofuran
4.2: 70 percent / NaBH4 / tetrahydrofuran; H2O
5.1: Dess-Martin reagent / benzene; CH2Cl2
6.1: 80 percent / benzene
7.1: 82 percent / HCl / H2O; tetrahydrofuran
8.1: MnO2 / benzene; CH2Cl2
8.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
8.3: 40 percent / Et3N / tetrahydrofuran
9.1: Dess-Martin reagent / benzene; CH2Cl2
9.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
10.1: HCl / H2O; methanol / 20 °C
View Scheme
Multi-step reaction with 16 steps
1.1: 92 percent / DDQ / CH2Cl2; H2O
2.1: MnO2 / CH2Cl2
3.1: 86 percent / BuLi; HMPA / tetrahydrofuran
4.1: DIBAH / tetrahydrofuran
4.2: 70 percent / NaBH4 / tetrahydrofuran; H2O
5.1: 93 percent / Na-Hg; Na2HPO4 / methanol
6.1: 96 percent / Et3N / CH2Cl2
7.1: 83 percent / 2,6-di-tert-butylpyridine / benzene
8.1: 81 percent / DIBAH / tetrahydrofuran
9.1: Dess-Martin reagent / benzene; CH2Cl2
10.1: 80 percent / benzene
11.1: 82 percent / HCl / H2O; tetrahydrofuran
12.1: MnO2 / benzene; CH2Cl2
12.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
12.3: 40 percent / Et3N / tetrahydrofuran
13.1: Dess-Martin reagent / benzene; CH2Cl2
13.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
14.1: HCl / H2O; methanol / 20 °C
View Scheme
(2E,6E,8Z)-(S)-10-(tert-Butyl-dimethyl-silanyloxy)-8-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-deca-2,6,8-trien-1-ol
808771-22-4

(2E,6E,8Z)-(S)-10-(tert-Butyl-dimethyl-silanyloxy)-8-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-deca-2,6,8-trien-1-ol

bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: MsCl; iPr2EtN; 4-DMAP / CH2Cl2
1.2: 81 percent / dimethylformamide
2.1: 86 percent / BuLi; HMPA / tetrahydrofuran
3.1: DIBAH / tetrahydrofuran
3.2: 70 percent / NaBH4 / tetrahydrofuran; H2O
4.1: Dess-Martin reagent / benzene; CH2Cl2
5.1: 80 percent / benzene
6.1: 82 percent / HCl / H2O; tetrahydrofuran
7.1: MnO2 / benzene; CH2Cl2
7.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
7.3: 40 percent / Et3N / tetrahydrofuran
8.1: Dess-Martin reagent / benzene; CH2Cl2
8.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
9.1: HCl / H2O; methanol / 20 °C
View Scheme
Multi-step reaction with 13 steps
1.1: MsCl; iPr2EtN; 4-DMAP / CH2Cl2
1.2: 81 percent / dimethylformamide
2.1: 86 percent / BuLi; HMPA / tetrahydrofuran
3.1: DIBAH / tetrahydrofuran
3.2: 70 percent / NaBH4 / tetrahydrofuran; H2O
4.1: 93 percent / Na-Hg; Na2HPO4 / methanol
5.1: 96 percent / Et3N / CH2Cl2
6.1: 83 percent / 2,6-di-tert-butylpyridine / benzene
7.1: 81 percent / DIBAH / tetrahydrofuran
8.1: Dess-Martin reagent / benzene; CH2Cl2
9.1: 80 percent / benzene
10.1: 82 percent / HCl / H2O; tetrahydrofuran
11.1: MnO2 / benzene; CH2Cl2
11.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
11.3: 40 percent / Et3N / tetrahydrofuran
12.1: Dess-Martin reagent / benzene; CH2Cl2
12.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
13.1: HCl / H2O; methanol / 20 °C
View Scheme
(R)-4-benzyl-3-((S,E)-6-(tert-butyldiphenylsilyloxy)-2-methylhex-4-enoyl)oxazolidin-2-one
808771-17-7

(R)-4-benzyl-3-((S,E)-6-(tert-butyldiphenylsilyloxy)-2-methylhex-4-enoyl)oxazolidin-2-one

bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: 92 percent / Et3N / PdCl2(PPh3)2 / methanol
2.1: MsCl; iPr2EtN; 4-DMAP / CH2Cl2
2.2: 81 percent / dimethylformamide
3.1: 86 percent / BuLi; HMPA / tetrahydrofuran
4.1: DIBAH / tetrahydrofuran
4.2: 70 percent / NaBH4 / tetrahydrofuran; H2O
5.1: Dess-Martin reagent / benzene; CH2Cl2
6.1: 80 percent / benzene
7.1: 82 percent / HCl / H2O; tetrahydrofuran
8.1: MnO2 / benzene; CH2Cl2
8.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
8.3: 40 percent / Et3N / tetrahydrofuran
9.1: Dess-Martin reagent / benzene; CH2Cl2
9.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
10.1: HCl / H2O; methanol / 20 °C
View Scheme
Multi-step reaction with 15 steps
1.1: 92 percent / Et3N / PdCl2(PPh3)2 / methanol
2.1: MsCl; iPr2EtN; 4-DMAP / CH2Cl2
2.2: 81 percent / dimethylformamide
3.1: 86 percent / BuLi; HMPA / tetrahydrofuran
4.1: DIBAH / tetrahydrofuran
4.2: 70 percent / NaBH4 / tetrahydrofuran; H2O
5.1: 93 percent / Na-Hg; Na2HPO4 / methanol
6.1: 96 percent / Et3N / CH2Cl2
7.1: 83 percent / 2,6-di-tert-butylpyridine / benzene
8.1: 81 percent / DIBAH / tetrahydrofuran
9.1: Dess-Martin reagent / benzene; CH2Cl2
10.1: 80 percent / benzene
11.1: 82 percent / HCl / H2O; tetrahydrofuran
12.1: MnO2 / benzene; CH2Cl2
12.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
12.3: 40 percent / Et3N / tetrahydrofuran
13.1: Dess-Martin reagent / benzene; CH2Cl2
13.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
14.1: HCl / H2O; methanol / 20 °C
View Scheme
{(2E,6E,8Z)-(S)-10-(tert-Butyl-dimethyl-silanyloxy)-8-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-deca-2,6,8-triene-1-sulfonyl}-benzene
808771-23-5

{(2E,6E,8Z)-(S)-10-(tert-Butyl-dimethyl-silanyloxy)-8-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-deca-2,6,8-triene-1-sulfonyl}-benzene

bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: 86 percent / BuLi; HMPA / tetrahydrofuran
2.1: DIBAH / tetrahydrofuran
2.2: 70 percent / NaBH4 / tetrahydrofuran; H2O
3.1: Dess-Martin reagent / benzene; CH2Cl2
4.1: 80 percent / benzene
5.1: 82 percent / HCl / H2O; tetrahydrofuran
6.1: MnO2 / benzene; CH2Cl2
6.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
6.3: 40 percent / Et3N / tetrahydrofuran
7.1: Dess-Martin reagent / benzene; CH2Cl2
7.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
8.1: HCl / H2O; methanol / 20 °C
View Scheme
Multi-step reaction with 12 steps
1.1: 86 percent / BuLi; HMPA / tetrahydrofuran
2.1: DIBAH / tetrahydrofuran
2.2: 70 percent / NaBH4 / tetrahydrofuran; H2O
3.1: 93 percent / Na-Hg; Na2HPO4 / methanol
4.1: 96 percent / Et3N / CH2Cl2
5.1: 83 percent / 2,6-di-tert-butylpyridine / benzene
6.1: 81 percent / DIBAH / tetrahydrofuran
7.1: Dess-Martin reagent / benzene; CH2Cl2
8.1: 80 percent / benzene
9.1: 82 percent / HCl / H2O; tetrahydrofuran
10.1: MnO2 / benzene; CH2Cl2
10.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
10.3: 40 percent / Et3N / tetrahydrofuran
11.1: Dess-Martin reagent / benzene; CH2Cl2
11.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
12.1: HCl / H2O; methanol / 20 °C
View Scheme
(2E,4Z,8Z,10E,14E,18E,20Z)-(6R,17S)-22-Hydroxy-20-(2-hydroxy-ethyl)-6-methoxy-2,5,17-trimethyl-docosa-2,4,8,10,14,18,20-heptaenoic acid tert-butyl ester
1027938-85-7

(2E,4Z,8Z,10E,14E,18E,20Z)-(6R,17S)-22-Hydroxy-20-(2-hydroxy-ethyl)-6-methoxy-2,5,17-trimethyl-docosa-2,4,8,10,14,18,20-heptaenoic acid tert-butyl ester

bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: MnO2 / benzene; CH2Cl2
1.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
1.3: 40 percent / Et3N / tetrahydrofuran
2.1: Dess-Martin reagent / benzene; CH2Cl2
2.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
3.1: HCl / H2O; methanol / 20 °C
View Scheme
(2Z,6Z,8E,12E,16E,18Z)-(4R,15S)-20-(tert-Butyl-dimethyl-silanyloxy)-18-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methoxy-3,15-dimethyl-icosa-2,6,8,12,16,18-hexaenal
808771-46-2

(2Z,6Z,8E,12E,16E,18Z)-(4R,15S)-20-(tert-Butyl-dimethyl-silanyloxy)-18-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methoxy-3,15-dimethyl-icosa-2,6,8,12,16,18-hexaenal

bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 80 percent / benzene
2.1: 82 percent / HCl / H2O; tetrahydrofuran
3.1: MnO2 / benzene; CH2Cl2
3.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
3.3: 40 percent / Et3N / tetrahydrofuran
4.1: Dess-Martin reagent / benzene; CH2Cl2
4.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
5.1: HCl / H2O; methanol / 20 °C
View Scheme
(2Z,6Z,8E,12E,16E,18Z)-(4R,15S)-20-(tert-Butyl-dimethyl-silanyloxy)-18-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methoxy-3,15-dimethyl-icosa-2,6,8,12,16,18-hexaen-1-ol
808771-33-7

(2Z,6Z,8E,12E,16E,18Z)-(4R,15S)-20-(tert-Butyl-dimethyl-silanyloxy)-18-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methoxy-3,15-dimethyl-icosa-2,6,8,12,16,18-hexaen-1-ol

bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: Dess-Martin reagent / benzene; CH2Cl2
2.1: 80 percent / benzene
3.1: 82 percent / HCl / H2O; tetrahydrofuran
4.1: MnO2 / benzene; CH2Cl2
4.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
4.3: 40 percent / Et3N / tetrahydrofuran
5.1: Dess-Martin reagent / benzene; CH2Cl2
5.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
6.1: HCl / H2O; methanol / 20 °C
View Scheme
(2Z,6Z,8E,12E,16E,18Z)-(4R,15S)-20-(tert-Butyl-dimethyl-silanyloxy)-18-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,15-dimethyl-icosa-2,6,8,12,16,18-hexaene-1,4-diol
808772-71-6

(2Z,6Z,8E,12E,16E,18Z)-(4R,15S)-20-(tert-Butyl-dimethyl-silanyloxy)-18-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,15-dimethyl-icosa-2,6,8,12,16,18-hexaene-1,4-diol

bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: 96 percent / Et3N / CH2Cl2
2.1: 83 percent / 2,6-di-tert-butylpyridine / benzene
3.1: 81 percent / DIBAH / tetrahydrofuran
4.1: Dess-Martin reagent / benzene; CH2Cl2
5.1: 80 percent / benzene
6.1: 82 percent / HCl / H2O; tetrahydrofuran
7.1: MnO2 / benzene; CH2Cl2
7.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
7.3: 40 percent / Et3N / tetrahydrofuran
8.1: Dess-Martin reagent / benzene; CH2Cl2
8.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
9.1: HCl / H2O; methanol / 20 °C
View Scheme
2,2-Dimethyl-propionic acid (2Z,6Z,8E,12E,16E,18Z)-(4R,15S)-20-(tert-butyl-dimethyl-silanyloxy)-18-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methoxy-3,15-dimethyl-icosa-2,6,8,12,16,18-hexaenyl ester
808771-45-1

2,2-Dimethyl-propionic acid (2Z,6Z,8E,12E,16E,18Z)-(4R,15S)-20-(tert-butyl-dimethyl-silanyloxy)-18-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methoxy-3,15-dimethyl-icosa-2,6,8,12,16,18-hexaenyl ester

bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 81 percent / DIBAH / tetrahydrofuran
2.1: Dess-Martin reagent / benzene; CH2Cl2
3.1: 80 percent / benzene
4.1: 82 percent / HCl / H2O; tetrahydrofuran
5.1: MnO2 / benzene; CH2Cl2
5.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
5.3: 40 percent / Et3N / tetrahydrofuran
6.1: Dess-Martin reagent / benzene; CH2Cl2
6.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
7.1: HCl / H2O; methanol / 20 °C
View Scheme
2,2-Dimethyl-propionic acid (2Z,6Z,8E,12E,16E,18Z)-(4R,15S)-20-(tert-butyl-dimethyl-silanyloxy)-18-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-hydroxy-3,15-dimethyl-icosa-2,6,8,12,16,18-hexaenyl ester
808772-72-7

2,2-Dimethyl-propionic acid (2Z,6Z,8E,12E,16E,18Z)-(4R,15S)-20-(tert-butyl-dimethyl-silanyloxy)-18-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-hydroxy-3,15-dimethyl-icosa-2,6,8,12,16,18-hexaenyl ester

bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: 83 percent / 2,6-di-tert-butylpyridine / benzene
2.1: 81 percent / DIBAH / tetrahydrofuran
3.1: Dess-Martin reagent / benzene; CH2Cl2
4.1: 80 percent / benzene
5.1: 82 percent / HCl / H2O; tetrahydrofuran
6.1: MnO2 / benzene; CH2Cl2
6.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
6.3: 40 percent / Et3N / tetrahydrofuran
7.1: Dess-Martin reagent / benzene; CH2Cl2
7.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
8.1: HCl / H2O; methanol / 20 °C
View Scheme
(R)-5-{(2Z,4E,8E,12E,14Z)-(S)-7-Benzenesulfonyl-16-(tert-butyl-dimethyl-silanyloxy)-14-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-11-methyl-hexadeca-2,4,8,12,14-pentaenyl}-4-methyl-5H-furan-2-one
808771-31-5

(R)-5-{(2Z,4E,8E,12E,14Z)-(S)-7-Benzenesulfonyl-16-(tert-butyl-dimethyl-silanyloxy)-14-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-11-methyl-hexadeca-2,4,8,12,14-pentaenyl}-4-methyl-5H-furan-2-one

bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: DIBAH / tetrahydrofuran
1.2: 70 percent / NaBH4 / tetrahydrofuran; H2O
2.1: Dess-Martin reagent / benzene; CH2Cl2
3.1: 80 percent / benzene
4.1: 82 percent / HCl / H2O; tetrahydrofuran
5.1: MnO2 / benzene; CH2Cl2
5.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
5.3: 40 percent / Et3N / tetrahydrofuran
6.1: Dess-Martin reagent / benzene; CH2Cl2
6.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
7.1: HCl / H2O; methanol / 20 °C
View Scheme
Multi-step reaction with 11 steps
1.1: DIBAH / tetrahydrofuran
1.2: 70 percent / NaBH4 / tetrahydrofuran; H2O
2.1: 93 percent / Na-Hg; Na2HPO4 / methanol
3.1: 96 percent / Et3N / CH2Cl2
4.1: 83 percent / 2,6-di-tert-butylpyridine / benzene
5.1: 81 percent / DIBAH / tetrahydrofuran
6.1: Dess-Martin reagent / benzene; CH2Cl2
7.1: 80 percent / benzene
8.1: 82 percent / HCl / H2O; tetrahydrofuran
9.1: MnO2 / benzene; CH2Cl2
9.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
9.3: 40 percent / Et3N / tetrahydrofuran
10.1: Dess-Martin reagent / benzene; CH2Cl2
10.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
11.1: HCl / H2O; methanol / 20 °C
View Scheme
(2E,4Z,8Z,10E,14E,18E,20Z)-(6R,17S)-22-(tert-Butyl-dimethyl-silanyloxy)-20-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6-methoxy-2,5,17-trimethyl-docosa-2,4,8,10,14,18,20-heptaenoic acid tert-butyl ester
808771-34-8

(2E,4Z,8Z,10E,14E,18E,20Z)-(6R,17S)-22-(tert-Butyl-dimethyl-silanyloxy)-20-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6-methoxy-2,5,17-trimethyl-docosa-2,4,8,10,14,18,20-heptaenoic acid tert-butyl ester

bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 82 percent / HCl / H2O; tetrahydrofuran
2.1: MnO2 / benzene; CH2Cl2
2.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
2.3: 40 percent / Et3N / tetrahydrofuran
3.1: Dess-Martin reagent / benzene; CH2Cl2
3.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
4.1: HCl / H2O; methanol / 20 °C
View Scheme
(2Z,6Z,8E,12E,16E,18Z)-(4R,15S)-11-Benzenesulfonyl-20-(tert-butyl-dimethyl-silanyloxy)-18-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,15-dimethyl-icosa-2,6,8,12,16,18-hexaene-1,4-diol

(2Z,6Z,8E,12E,16E,18Z)-(4R,15S)-11-Benzenesulfonyl-20-(tert-butyl-dimethyl-silanyloxy)-18-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3,15-dimethyl-icosa-2,6,8,12,16,18-hexaene-1,4-diol

bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: Dess-Martin reagent / benzene; CH2Cl2
2.1: 80 percent / benzene
3.1: 82 percent / HCl / H2O; tetrahydrofuran
4.1: MnO2 / benzene; CH2Cl2
4.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
4.3: 40 percent / Et3N / tetrahydrofuran
5.1: Dess-Martin reagent / benzene; CH2Cl2
5.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
6.1: HCl / H2O; methanol / 20 °C
View Scheme
Multi-step reaction with 10 steps
1.1: 93 percent / Na-Hg; Na2HPO4 / methanol
2.1: 96 percent / Et3N / CH2Cl2
3.1: 83 percent / 2,6-di-tert-butylpyridine / benzene
4.1: 81 percent / DIBAH / tetrahydrofuran
5.1: Dess-Martin reagent / benzene; CH2Cl2
6.1: 80 percent / benzene
7.1: 82 percent / HCl / H2O; tetrahydrofuran
8.1: MnO2 / benzene; CH2Cl2
8.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
8.3: 40 percent / Et3N / tetrahydrofuran
9.1: Dess-Martin reagent / benzene; CH2Cl2
9.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
10.1: HCl / H2O; methanol / 20 °C
View Scheme
(2E,4Z,8Z,10E,14E,18E,20Z)-(6R,17S)-20-(2-Hydroxy-ethyl)-6-methoxy-2,5,17-trimethyl-docosa-2,4,8,10,14,18,20-heptaenedioic acid 1-tert-butyl ester 22-(tert-butyl-diphenyl-silanyloxymethyl) ester
808771-35-9

(2E,4Z,8Z,10E,14E,18E,20Z)-(6R,17S)-20-(2-Hydroxy-ethyl)-6-methoxy-2,5,17-trimethyl-docosa-2,4,8,10,14,18,20-heptaenedioic acid 1-tert-butyl ester 22-(tert-butyl-diphenyl-silanyloxymethyl) ester

bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: Dess-Martin reagent / benzene; CH2Cl2
1.2: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O
2.1: HCl / H2O; methanol / 20 °C
View Scheme
dimethyl 3-methyl-2-trans-pentenedioate
81061-92-9

dimethyl 3-methyl-2-trans-pentenedioate

bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) lithium diisopropylamide, hexamethylphosphoric triamide / 1.) THF, -78 - 0 deg C, 1 h, 2.) -40 - 0 deg C, 20 min
3: 2.) tetra-n-butylammonium hydroxide / 1.) Lindlar reduction, 2.) methanol, water, 23 deg C, 30 min
4: 65 percent / potassium methoxide / tetrahydrofuran; methanol / 0.08 h / 0 °C
View Scheme
(E)-(S)-2-Methyl-non-4-en-8-ynal
88303-96-2

(E)-(S)-2-Methyl-non-4-en-8-ynal

bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) lithium diisopropylamide, hexamethylphosphoric triamide / 1.) THF, -78 - 0 deg C, 1 h, 2.) -40 - 0 deg C, 20 min
3: 2.) tetra-n-butylammonium hydroxide / 1.) Lindlar reduction, 2.) methanol, water, 23 deg C, 30 min
4: 65 percent / potassium methoxide / tetrahydrofuran; methanol / 0.08 h / 0 °C
View Scheme
(E)-(S)-2-Methyl-non-4-en-8-yn-1-ol
88304-00-1

(E)-(S)-2-Methyl-non-4-en-8-yn-1-ol

bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: pyridinium chlorochromate, neutral alumina / CH2Cl2 / 1.5 h / 23 °C
2: 1.) lithium diisopropylamide, hexamethylphosphoric triamide / 1.) THF, -78 - 0 deg C, 1 h, 2.) -40 - 0 deg C, 20 min
4: 2.) tetra-n-butylammonium hydroxide / 1.) Lindlar reduction, 2.) methanol, water, 23 deg C, 30 min
5: 65 percent / potassium methoxide / tetrahydrofuran; methanol / 0.08 h / 0 °C
View Scheme
(R)-1-(S)-Oxiranyl-4-triisopropylsilanyl-but-3-yn-1-ol
88304-15-8

(R)-1-(S)-Oxiranyl-4-triisopropylsilanyl-but-3-yn-1-ol

bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: 96 percent / sodium hydride / tetrahydrofuran / 20 °C
2: 81 percent / ethanol / 10 h / 35 °C
3: 93 percent / diisopropylcarbodiimide, dimethyl sulfoxide, dichloroacetic acid / 0.5 h / 0 °C
4: 1.) sodium hydride / 1.) ether, 23 deg C, 2.) 0 deg C, 10 min
5: sodium hydride, ether, Me2SO / 0.5 h / 0 °C
6: 86 percent / tetrahydrofuran / 0.17 h / -78 °C
7: 88 percent / diisobutylaluminum hydride / CH2Cl2 / 0.08 h / -78 °C
8: 96 percent / tetrahydrofuran / 4 h / 23 °C
9: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 23 °C
10: 1.) silver trifluoroacetate, triethylamine, 2.) bromine / 1.) 20 deg C, 2.) -78 deg C
12: 2.) tetra-n-butylammonium hydroxide / 1.) Lindlar reduction, 2.) methanol, water, 23 deg C, 30 min
13: 65 percent / potassium methoxide / tetrahydrofuran; methanol / 0.08 h / 0 °C
View Scheme
(2E,4Z)-(R)-6-Methoxy-2,5-dimethyl-nona-2,4-dien-8-ynoic acid ethyl ester
88303-97-3

(2E,4Z)-(R)-6-Methoxy-2,5-dimethyl-nona-2,4-dien-8-ynoic acid ethyl ester

bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) silver trifluoroacetate, triethylamine, 2.) bromine / 1.) 20 deg C, 2.) -78 deg C
3: 2.) tetra-n-butylammonium hydroxide / 1.) Lindlar reduction, 2.) methanol, water, 23 deg C, 30 min
4: 65 percent / potassium methoxide / tetrahydrofuran; methanol / 0.08 h / 0 °C
View Scheme
bongkrekic acid
11076-19-0

bongkrekic acid

methyl (2E,4Z,6R,8Z,10E,14E,17S,18E,20Z)-17-methoxy-21-methoxycarbonyl-3-methoxycarbonylmethyl-6,18-dimethylcosa-2,4,8,12,14,18,20-heptaenoate
42415-59-8

methyl (2E,4Z,6R,8Z,10E,14E,17S,18E,20Z)-17-methoxy-21-methoxycarbonyl-3-methoxycarbonylmethyl-6,18-dimethylcosa-2,4,8,12,14,18,20-heptaenoate

Conditions
ConditionsYield
In diethyl ether at 0℃; for 0.5h; Inert atmosphere;100%
In diethyl ether
bongkrekic acid
11076-19-0

bongkrekic acid

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

methyl (2E,4Z,6R,8Z,10E,14E,17S,18E,20Z)-17-methoxy-21-methoxycarbonyl-3-methoxycarbonylmethyl-6,18-dimethylcosa-2,4,8,12,14,18,20-heptaenoate
42415-59-8

methyl (2E,4Z,6R,8Z,10E,14E,17S,18E,20Z)-17-methoxy-21-methoxycarbonyl-3-methoxycarbonylmethyl-6,18-dimethylcosa-2,4,8,12,14,18,20-heptaenoate

Conditions
ConditionsYield
In methanol; diethyl ether; dichloromethane at 20℃; for 0.666667h;100%
bongkrekic acid
11076-19-0

bongkrekic acid

Conditions
ConditionsYield
With diazomethyl-trimethyl-silane In methanol; diethyl ether; dichloromethane at 20℃; for 0.666667h;100%

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