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Simagchem Corporation

Welcome to Simagchem, your partner in China as a premier supply of bulk specialty chemicals for industry and life science. We introduce experienced quality product and exceptional JIT service with instant market intelligence in China to benefit our

Xi'an Xszo Chem Co., Ltd.

1. Factory price and high quality must be guaranteed, base on 8 years of production and R&D experience2. Free samples will be provided,ensure specifications and quality are right for customer3. Customers will receive the most professional technical s

Factory Price API 99% Epothilone D 189453-10-9 GMP Manufacturer

Cas:189453-10-9

Min.Order:1 Gram

FOB Price: $0.1

Type:Manufacturers

inquiry

Dayang Chem (Hangzhou) Co.,Ltd.

As a leading manufacturer and supplier of chemicals in China, DayangChem not only supply popular chemicals, but also DayangChem's R&D center offer custom synthesis services. DayangChem can provide different quantities of custom synthesis ch

EPOTHILONE D

Cas:189453-10-9

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

inquiry

Chemwill Asia Co., Ltd.

Our 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

Epothilone D

Cas:189453-10-9

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

inquiry

Hebei Nengqian Chemical Import and Export Co., LTD

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

Epothilone D

Cas:189453-10-9

Min.Order:1 Kilogram

FOB Price: $9.0 / 99.0

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

New production CAS 189453-10-9 with best quality

Cas:189453-10-9

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

Epothilone D

Cas:189453-10-9

Min.Order:1 Kilogram

FOB Price: $5.0 / 10.0

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

Xi'an Faithful Biotech Co., Ltd.

We are the manufacturers and suppliers of API in China, and warehouse in Germany and USA of California, which can quickly and safely deliver to your address 1.High quality and competitive price. 2.Free sample for your evaluation. 3.Promptly delivery

Leader Biochemical Group

About Product Details Items Specifications Test Results Appearance White to white crystalline powde

China Biggest Factory Manufacturer Supply Epothilone D CAS 189453-10-9

Cas:189453-10-9

Min.Order:100 Kilogram

FOB Price: $1.0 / 2.0

Type:Lab/Research institutions

inquiry

Qingdao Beluga Import and Export Co., LTD

Epothilone D CAS:189453-10-9 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 intermediat

Epothilone D CAS:189453-10-9

Cas:189453-10-9

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

Taizhou Crene Biotechnology co.ltd

Our 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-

Epothilone D 189453-10-9

Cas:189453-10-9

Min.Order:100 Milligram

Negotiable

Type:Lab/Research institutions

inquiry

Hubei Jiutian Bio-medical Technology Co., Ltd

1,we produce and sell good chemicals around the world. 2,our success rate is about 95%. this means, if customer order is accepted, the probability that the customer will obtain the ordered substances, is 95%. 3,our staff consists of highly qualifie

cas 189453-10-9 cas 189453-10-9 Epothilone D

Cas:189453-10-9

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Afine Chemicals Limited

Our Services 1. New Molecules R&D 2. Own test center HPLC NMR GC LC-MS 3. API and Intermediates from China reputed manufacturers 4. Documents support COA MOA MSDS DMF open part Our advantages 1. Government awarded company. Top 100 enter

afine-EPOTHILONE D

Cas:189453-10-9

Min.Order:0

Negotiable

Type:Lab/Research institutions

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

TaiChem Taizhou Limited

Established in May 2015, TaiChem Ltd. is initially invested by a British research and development company and started by PhDs back from aboard. The company is registered in China Medical City (CMC), Taizhou, Jiangsu Province, and the production site

Epothilone D

Cas:189453-10-9

Min.Order:10 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Xiamen Jenny Chemical Technology Co., Ltd.

GMP 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,

EpothiloneD

Cas:189453-10-9

Min.Order:1 Milligram

Negotiable

Type:Trading Company

inquiry

SAGECHEM LIMITED

SAGECHEM is a chemical R&D, manufacturing and distribution company in China since 2009, including pharmaceutical intermediates, agrochemical, dyestuff intermediates, organosilicone, API and etc. We also offer a full range of services in custom synthe

SAGECHEM/Epothilone D/SAGECHEM/Manufacturer in China

Cas:189453-10-9

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Sinoway Industrial Co., Ltd.

Why is SINOWAY:1) Specialized in pharmaceutical and healthcare industrial since 19872) ISO 9001:2015 & SGS audited supplier . 3) Accept various payment terms : T.T 30-60 days.4) We have warehouse in USA with quickly shipment .5) We can do different t

99% up by HPLC Epothilone D 189453-10-9

Cas:189453-10-9

Min.Order:0

Negotiable

Type:Trading Company

inquiry

HANGZHOU YUNUO CHEMICAL CO.,LTD

Superior quality, moderate price & quick delivery. Appearance:NA Storage:Sealed in a cool ,dry and microtherm place , avoid light . Package: 1g/bag, 5g/bag, 10g/bag, 100g/bag, 1kg/bag or as per your request Application:It is an important raw m

Epo D

Cas:189453-10-9

Min.Order:1 Gram

Negotiable

Type:Trading Company

inquiry

Shanghai Acmec Biochemical Technology Co., Ltd.

Acmec is a leading manufacturer and supplier of biochemical reagents and life science products. We have over 40,000 items in stock (real-time inventory) and offer discounted prices to registered members of the online store ( www.acmec.com.cn ) Appea

Acmec Epothilone D 100mg

Cas:189453-10-9

Min.Order:1 bottle

Negotiable

Type:Lab/Research institutions

inquiry

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

Epothilone D

Cas:189453-10-9

Min.Order:0

Negotiable

Type:Manufacturers

inquiry

Aecochem Corp.

Our clients, like BASF,CHEMO,Brenntag,ASR,Evonik,Merck and etc.Appearance:COA Storage:in stock Application:MSDS/TDS

Hubei Taiho Chemical Co.,LTD

TAIHO Unique Advantages:1.We're factory2.Free samples available3.Commodity inspection can be done4.ISO9001,Kosher certifications5.10 years experiences Storage:Store in cool &dry place Package:aluminium foil bag/fiber can/plastic drum Application:comp

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

Epothilone D

Cas:189453-10-9

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.

Enke Pharma-tech Co.,Ltd. (Cangzhou, China )

high purity Storage:normal temperature Package:DRUM Application:mainly for medical use for R&Dpurpose use only Transportation:AIR,SEA Port:BEIJING,SHANGHAI,TIANJIN,SHENZHEN

Epothilone D

Cas:189453-10-9

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Synthetic route

12,13-deoxy-3-(triethylsilyloxy)epothilone B
241129-41-9

12,13-deoxy-3-(triethylsilyloxy)epothilone B

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
With pyridine hydrogenfluoride In tetrahydrofuran98%
With pyridine hydrogenfluoride In tetrahydrofuran at 0℃; for 5h;91%
(4S,7R,8S,9S,13Z,16S)-4,8-bis{[tert-butyl(dimethyl)silyl]oxy}-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]oxacyclohexadec-13-ene-2,6-dione
189453-35-8

(4S,7R,8S,9S,13Z,16S)-4,8-bis{[tert-butyl(dimethyl)silyl]oxy}-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]oxacyclohexadec-13-ene-2,6-dione

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
With pyridine hydrogenfluoride In tetrahydrofuran at 20℃; for 36h;96%
With pyridine; pyridine hydrogenfluoride In tetrahydrofuran at 0 - 20℃; for 36h;96%
With pyridine hydrogenfluoride In tetrahydrofuran92%
(13Z,4S,7R,8S,9S,16S)-4-(tert-butyldimethylsilyloxy)-8-hydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methylthiazol-4-yl)vinyl]oxacyclohexadec-13-ene-2,6-dione
219823-99-1

(13Z,4S,7R,8S,9S,16S)-4-(tert-butyldimethylsilyloxy)-8-hydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methylthiazol-4-yl)vinyl]oxacyclohexadec-13-ene-2,6-dione

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
With pyridine hydrogenfluoride In tetrahydrofuran at 20℃; for 16h;95%
With trifluoroacetic acid In dichloromethane at 0℃; for 1.5h;69%
(Z)-(4S,6R,7S,8S,9S,16S)-8-(tert-Butyl-dimethyl-silanyloxy)-4,6-dihydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-oxacyclohexadec-13-en-2-one
189453-51-8

(Z)-(4S,6R,7S,8S,9S,16S)-8-(tert-Butyl-dimethyl-silanyloxy)-4,6-dihydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-oxacyclohexadec-13-en-2-one

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
With pyridine hydrogenfluoride In tetrahydrofuran at 0 - 20℃; for 2h; desilylation;92%
Multi-step reaction with 3 steps
1: 89 percent / 2,6-lutidine / CH2Cl2 / -30 °C
2: 67 percent / Dess-Martin periodinane / CH2Cl2 / Ambient temperature
3: 80 percent / HF*pyridine / tetrahydrofuran / Ambient temperature
View Scheme
Carbonic acid (Z)-(4S,7R,8S,9S,16S)-4-hydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-2,6-dioxo-oxacyclohexadec-13-en-8-yl ester 2,2,2-trichloro-ethyl ester
380605-94-7

Carbonic acid (Z)-(4S,7R,8S,9S,16S)-4-hydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-2,6-dioxo-oxacyclohexadec-13-en-8-yl ester 2,2,2-trichloro-ethyl ester

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
With ammonium chloride; zinc In methanol Heating;92%
(E)-9,10-dehydro-12,13-desoxyepothilone B
350493-61-7

(E)-9,10-dehydro-12,13-desoxyepothilone B

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
With TrisNHNH2; triethylamine In 1,2-dichloro-ethane at 50℃; for 7h;91%
With TrisNHNH2; triethylamine In 1,2-dichloro-ethane at 50℃; for 7h;91%
With potassium diazodicarboxylate; acetic acid In 1,2-dichloro-ethane at 45℃;60%
10,11-didehydroepothilone D
371979-40-7

10,11-didehydroepothilone D

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
With potassium diazodicarboxylate; acetic acid In dichloromethane Heating;86%
epothilone B
152044-54-7

epothilone B

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
With n-butyllithium; tungsten(VI) chloride In tetrahydrofuran deoxygenation;78%
7-[(1E)-1-methyl-2-(2-methyl(1,3-thiazol-4-yl))vinyl]-(3S,7S,14S,15S,16R)-3,15-dihydroxy-2,2,10,14,16-pentamethyl-6-oxacyclohexadeca-9,12-diene-1,5-dione
220889-57-6

7-[(1E)-1-methyl-2-(2-methyl(1,3-thiazol-4-yl))vinyl]-(3S,7S,14S,15S,16R)-3,15-dihydroxy-2,2,10,14,16-pentamethyl-6-oxacyclohexadeca-9,12-diene-1,5-dione

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
With trisylhydrazine; triethylamine In diethyl ether at 39℃;71%
With trisylhydrazine; triethylamine In 1,2-dichloro-ethane at 50℃; for 18h;70%
With potassium diazodicarboxylate; acetic acid In dichloromethane for 24h; Heating;52%
With potassium diazodicarboxylate; acetic acid In dichloromethane for 25h; Heating;52%
(Z)-(4S,7R,8S,9S,16S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-oxacyclohexadec-13-ene-2,6-dione
204195-20-0

(Z)-(4S,7R,8S,9S,16S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-oxacyclohexadec-13-ene-2,6-dione

A

epothilone D
189453-10-9

epothilone D

B

E-epothilone D
189453-40-5

E-epothilone D

Conditions
ConditionsYield
With pyridine hydrogenfluoride In tetrahydrofuran at 20℃; for 1.5h; desilylation;
With trifluoroacetic acid In dichloromethane at 0 - 20℃;
With pyridine; hydrogen fluoride In tetrahydrofuran at 20℃;
(3S,6R,7S,8S,12Z,15S,16E)-3-(tert-butyldimethylsilyloxy)-7-hydroxy-15-(2-trimethylsilylethoxymethoxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid
823789-81-7

(3S,6R,7S,8S,12Z,15S,16E)-3-(tert-butyldimethylsilyloxy)-7-hydroxy-15-(2-trimethylsilylethoxymethoxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: pyridine / CH2Cl2 / 1 h / 0 °C
2.1: CH2Cl2 / 5 h / 20 °C
3.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
4.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
5.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
5.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
6.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
7.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme
(12Z,16E)-(3S,6R,7S,8S,15S)-3-(tert-Butyl-dimethyl-silanyloxy)-15-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-heptadeca-12,16-dienoic acid
380605-92-5

(12Z,16E)-(3S,6R,7S,8S,15S)-3-(tert-Butyl-dimethyl-silanyloxy)-15-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-heptadeca-12,16-dienoic acid

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
1.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
2.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
3.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme
C45H85NO7SSi3

C45H85NO7SSi3

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: CH2Cl2 / 5 h / 20 °C
2.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
3.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
4.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
4.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
5.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
6.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme
(3S,6R,7S,8S,12Z,15S,16E)-3-(tert-butyldimethylsilyloxy)-7-[(2,2,2-trichloroethoxycarbonyl)oxy]-15-(2-trimethylsilylethoxymethoxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid
823789-87-3

(3S,6R,7S,8S,12Z,15S,16E)-3-(tert-butyldimethylsilyloxy)-7-[(2,2,2-trichloroethoxycarbonyl)oxy]-15-(2-trimethylsilylethoxymethoxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
2.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
2.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
3.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
4.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme
C48H86Cl3NO9SSi3

C48H86Cl3NO9SSi3

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
2.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
3.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
3.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
4.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
5.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme
4-(hydroxymethyl)-2-methylthiazole
76632-23-0

4-(hydroxymethyl)-2-methylthiazole

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: 85 percent / Ph3P; CBr4 / CCl4 / 3 h / 20 °C
2.1: 86 percent / 3 h / 160 °C
3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
3.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C
4.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C
4.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C
5.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C
6.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C
6.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C
7.1: pyridine / CH2Cl2 / 1 h / 0 °C
8.1: CH2Cl2 / 5 h / 20 °C
9.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
10.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
11.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
11.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
12.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
13.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme
4-(chloromethyl)-2-methyl-1,3-thiazole
39238-07-8

4-(chloromethyl)-2-methyl-1,3-thiazole

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: 86 percent / 6 h / 160 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
2.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C
3.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C
3.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C
4.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C
5.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C
5.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C
6.1: pyridine / CH2Cl2 / 1 h / 0 °C
7.1: CH2Cl2 / 5 h / 20 °C
8.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
9.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
10.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
10.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
11.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
12.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme
Multi-step reaction with 11 steps
1.1: 84 percent / 2 h / 165 °C
2.1: tBuOK / tetrahydrofuran
2.2: 75 percent / tetrahydrofuran / 4 h / -30 - 20 °C
3.1: AcOH; H2O / tetrahydrofuran / 24 h / 20 °C
4.1: NaBH4 / methanol
5.1: CBr4; PPh3 / acetonitrile / 0 °C
5.2: 91 percent / 2,6-di-tert-butyl-4-methylpyridine / acetonitrile / -40 °C
6.1: tetrahydrofuran / -78 °C
7.1: LiHMDS / tetrahydrofuran / -78 °C
7.2: 80 percent / tetrahydrofuran
8.1: TMSOTf; collidine / CH2Cl2 / 1 h / 0 °C
8.2: 85 percent / nBu4NF / tetrahydrofuran
9.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 1 h / 20 °C
9.2: 60 percent / DMAP / toluene / 80 °C
10.1: 86 percent / TFA / CH2Cl2 / 0 °C
11.1: 71 percent / 2,4,6-triisopropylbenzenesulfonyl hydrazide; Et3N / diethyl ether / 39 °C
View Scheme
Multi-step reaction with 18 steps
1.1: 97 percent / benzene / 8 h / Heating
2.1: 10.95 g / LiHMDS / tetrahydrofuran / 0.67 h / 55 °C
3.1: oxalyl chloride; DMSO; DIPEA / CH2Cl2 / -78 - 20 °C
4.1: KHMDS; 18-crown-6 / tetrahydrofuran / 0.25 h
4.2: 5.45 g / tetrahydrofuran / 0.5 h / -78 °C
5.1: 98 percent / DIBALH / tetrahydrofuran; heptane / 2.5 h / 0 °C
6.1: Ph3P; imidazole; I2 / acetonitrile; diethyl ether / 1 h / 20 °C
7.1: 18-crown-6; KHMDS / tetrahydrofuran / 1 h / -78 °C
7.2: 93 percent / tetrahydrofuran / 1 h / -78 °C
8.1: 65 percent / Na2HPO4; Na-Hg amalgam / methanol; tetrahydrofuran / -15 - 20 °C
9.1: 99 percent / CSA / methanol; CH2Cl2 / 5 h / 0 - 10 °C
10.1: Dess-Martin periodinane; pyridine / CH2Cl2 / 4 h / 20 °C
11.1: LDA / tetrahydrofuran / 1 h / -78 - -35 °C
11.2: tetrahydrofuran / 1.5 h / -95 - -80 °C
12.1: 99 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C
13.1: 87 percent / CSA / methanol; CH2Cl2 / 4 h / 0 °C
14.1: Dess-Martin periodinane; Py / CH2Cl2 / 2 h / 20 °C
15.1: 380 mg / NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; various solvent(s); H2O / 3 h
16.1: 55 percent / TBAF / tetrahydrofuran / 10 h / 20 °C
17.1: 69 percent / N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide *HCl; DMAP; DMAP*HCl / CHCl3 / 17 h / Heating
18.1: 96 percent / HF*Py; Py / tetrahydrofuran / 36 h / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: 4 h / Reflux
2.1: potassium hexamethylsilazane / tetrahydrofuran / 0.25 h / 0 °C
2.2: 2 h / -78 - -20 °C
3.1: trifluoroacetic acid / dichloromethane / 1 h / 0 °C
View Scheme
ethyl 2-methylthiazole-4-carboxylate
6436-59-5

ethyl 2-methylthiazole-4-carboxylate

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1.1: 84 percent / LiAlH4 / diethyl ether / 3 h / -78 °C
2.1: 85 percent / Ph3P; CBr4 / CCl4 / 3 h / 20 °C
3.1: 86 percent / 3 h / 160 °C
4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
4.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C
5.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C
5.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C
6.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C
7.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C
7.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C
8.1: pyridine / CH2Cl2 / 1 h / 0 °C
9.1: CH2Cl2 / 5 h / 20 °C
10.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
11.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
12.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
12.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
13.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
14.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme
Multi-step reaction with 23 steps
1: 90 percent / DIBAL / CH2Cl2 / 1 h / -78 °C
2: 98 percent / benzene / 2 h / Heating
3: 74 percent / diethyl ether; pentane / 1 h / -100 °C
4: 99 percent / imidazole / dimethylformamide / 1) 0 deg C, 45 min, 2) 25 deg C, 2.5 h
5: 95 percent / 4-methylmorpholine N-oxide, OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 1) 0 deg C, 2.5 h, 2) 25 deg C, 12 h
6: 98 percent / Pb(OAc)4 / ethyl acetate / 0.25 h / 0 °C
7: 95 percent / benzene / 3 h / Heating
8: 98 percent / DIBAL / tetrahydrofuran; CH2Cl2 / 3 h / -78 °C
9: 83 percent / Ph3P, CCl4 / 24 h / 100 °C
10: 99 percent / LiEt3BH / tetrahydrofuran / 1 h / 0 °C
11: 91 percent / 9-BBN / tetrahydrofuran / 2 h / 0 °C
12: 92 percent / I2, imidazole, Ph3P / diethyl ether; acetonitrile / 0.5 h / 0 °C
13: 1) LDA / 1) THF, 0 deg C, 8 h, 2) THF, -100 deg C -> -20 deg C, 10 h
14: 80 percent / monoperoxyphthalic acid magnesium salt / methanol / 1 h / 0 °C
15: 82 percent / DIBAL / toluene / 1 h / -78 °C
16: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min
17: 96 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C
18: 85 percent / camphorsulfonic acid / CH2Cl2; methanol / 0.5 h / 0 - 25 °C
19: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 30 min, 2) CH2Cl2, -78 deg C -> 0 deg C, 30 min
20: 90 percent / NaClO2, isobutylene, NaH2PO4 / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 1 h / Ambient temperature
21: 73 percent / TBAF / tetrahydrofuran / 8 h / 25 °C
22: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-DMAP / 1) THF, 25 deg C, 15 min, 2) toluene, 25 deg C, 12 h
23: 91 percent / CF3CO2H / CH2Cl2 / 1) -20 deg C -> 0 deg C, 2) 0 deg C, 1 h
View Scheme
diethyl (2-methyl-1,3-thiazol-4-yl)methylphosphonate
63928-37-0

diethyl (2-methyl-1,3-thiazol-4-yl)methylphosphonate

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
1.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C
2.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C
2.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C
3.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C
4.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C
4.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C
5.1: pyridine / CH2Cl2 / 1 h / 0 °C
6.1: CH2Cl2 / 5 h / 20 °C
7.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
8.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
9.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
9.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
10.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
11.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme
Multi-step reaction with 10 steps
1.1: tBuOK / tetrahydrofuran
1.2: 75 percent / tetrahydrofuran / 4 h / -30 - 20 °C
2.1: AcOH; H2O / tetrahydrofuran / 24 h / 20 °C
3.1: NaBH4 / methanol
4.1: CBr4; PPh3 / acetonitrile / 0 °C
4.2: 91 percent / 2,6-di-tert-butyl-4-methylpyridine / acetonitrile / -40 °C
5.1: tetrahydrofuran / -78 °C
6.1: LiHMDS / tetrahydrofuran / -78 °C
6.2: 80 percent / tetrahydrofuran
7.1: TMSOTf; collidine / CH2Cl2 / 1 h / 0 °C
7.2: 85 percent / nBu4NF / tetrahydrofuran
8.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 1 h / 20 °C
8.2: 60 percent / DMAP / toluene / 80 °C
9.1: 86 percent / TFA / CH2Cl2 / 0 °C
10.1: 71 percent / 2,4,6-triisopropylbenzenesulfonyl hydrazide; Et3N / diethyl ether / 39 °C
View Scheme
Multi-step reaction with 11 steps
1: 74 percent / n-BuLi
2: DIBAL-H
3: Dess-Martin periodinane
4: 67 percent / Li(i-Pr)2N / -78 °C
5: 79 percent / Cl2CHCO2H
6: Dess-Martin periodinane
7: NaClO2
8: MgBr2; n-BuSH; K2CO3
9: 62 percent / 2,4,6-trichlorobenzoyl chloride; DMAP
10: 91 percent / CF3CO2H / CH2Cl2
View Scheme
2,2-dimethyl-3-oxopentanal
106921-60-2

2,2-dimethyl-3-oxopentanal

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: 88 percent / Bu2BOTf; DIPEA / CH2Cl2 / 1 h / -78 °C
2.1: 95 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
3.1: 76 percent / lithium hydroxide; hydrogen peroxide / tetrahydrofuran; H2O / 4 h / 20 °C
4.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C
4.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C
5.1: pyridine / CH2Cl2 / 1 h / 0 °C
6.1: CH2Cl2 / 5 h / 20 °C
7.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
8.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
9.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
9.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
10.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
11.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme
Multi-step reaction with 14 steps
1.1: 68 percent / (-)-Ipc2BOMe / diethyl ether / -100 °C
2.1: i-Pr2NH; n-BuLi / tetrahydrofuran; hexane / 0.83 h / -78 °C
2.2: 61 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C
3.1: 89 percent / Et3N / CH2Cl2 / 0.75 h / 0 °C
4.1: OsO4; NaIO4 / tetrahydrofuran; H2O / 18 h
5.1: NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 1 h
6.1: 502 mg / methanol; benzene; hexane / 0.75 h
7.1: 92 percent / H2 / Pd/C / ethanol / 0.75 h
8.1: 99 percent / TPAP; NMO / CH2Cl2 / 1 h
9.1: hexamethyldisilazane; n-BuLi / tetrahydrofuran; hexane / -78 - -30 °C
9.2: 82 percent / tetrahydrofuran; hexane / 70 h / -78 - 20 °C
10.1: 66 percent / aq. NaOH / propan-2-ol / 16 h / 45 °C
11.1: 89 percent / TBAF / tetrahydrofuran / 16 h / 0 - 25 °C
12.1: 1,3,5-Cl3C6H2COCl; Et3N / tetrahydrofuran / 0.75 h / 0 °C
12.2: 63 percent / DMAP / toluene; tetrahydrofuran / 4.5 h / 75 °C
13.1: 83 percent / TFA / CH2Cl2 / 4.5 h / 0 °C
14.1: 52 percent / KO2CN=NCO2K; AcOH / CH2Cl2 / 25 h / Heating
View Scheme
Multi-step reaction with 16 steps
1.1: 68 percent / (-)-Ipc2BOMe / diethyl ether / -100 °C
2.1: i-Pr2NH; n-BuLi / tetrahydrofuran; hexane / 0.83 h / -78 °C
2.2: 61 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C
3.1: 89 percent / Et3N / CH2Cl2 / 0.75 h / 0 °C
4.1: OsO4; NaIO4 / tetrahydrofuran; H2O / 18 h
5.1: NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 1 h
6.1: 502 mg / methanol; benzene; hexane / 0.75 h
7.1: 92 percent / H2 / Pd/C / ethanol / 0.75 h
8.1: 99 percent / TPAP; NMO / CH2Cl2 / 1 h
9.1: t-BuOK / tetrahydrofuran / 5 h / -78 °C
9.2: 80 percent / tetrahydrofuran / 12 h / -78 °C
10.1: CuI; Et3N / diethyl ether; dimethylformamide / 20 °C
10.2: 60 percent / diethyl ether; dimethylformamide / 18 h / 20 °C
11.1: 68 percent / H2; Pb(OAc)2 / Pd/CaCO3 / hexane / 28 h / 20 °C
12.1: 66 percent / aq. NaOH / propan-2-ol / 16 h / 45 °C
13.1: 89 percent / TBAF / tetrahydrofuran / 16 h / 0 - 25 °C
14.1: 1,3,5-Cl3C6H2COCl; Et3N / tetrahydrofuran / 0.75 h / 0 °C
14.2: 63 percent / DMAP / toluene; tetrahydrofuran / 4.5 h / 75 °C
15.1: 83 percent / TFA / CH2Cl2 / 4.5 h / 0 °C
16.1: 52 percent / KO2CN=NCO2K; AcOH / CH2Cl2 / 25 h / Heating
View Scheme
Multi-step reaction with 6 steps
1.1: Bu2BOTf; DIPEA / CH2Cl2 / -78 - 0 °C
1.2: 70 percent / Raney Ni / acetone / 0.75 h / 60 °C
2.1: 2,6-lutidine / CH2Cl2 / 0 - 20 °C
2.2: LiOH; H2O2 / tetrahydrofuran; H2O / 20 °C
3.1: 2,4,6-Cl3C6H2COCl; TEA; DMAP / tetrahydrofuran; toluene / 1 h / 20 °C
4.1: 95 percent / HF / pyridine; CH2Cl2 / 20 °C
5.1: 92 percent / Zn; aq. NH4Cl / methanol / Heating
View Scheme
Multi-step reaction with 13 steps
1: 74 percent / diethyl ether / 0.5 h / -100 °C
2: 98 percent / 2,6-lutidine / CH2Cl2 / 0.75 h / -78 °C
3: 1) O3, 2) PPh3 / 1) CH2Cl2, -78 deg C, 30 min, 2) Ch2Cl2, -78 deg C -> room temperature; room temperature, 1 h
4: lithium tri-tert-butoxyaluminohydride / tetrahydrofuran / 1) -78 deg C, 5 min, 2) 0 deg C, 15 min
5: 1.26 g / Et3N, 4-DMAP / CH2Cl2 / 1) 0 deg C, 2 h, 2) 25 deg C, 10 h
6: 1) LDA / 1) THF, -78 deg C, 15 min; -78 deg C -> -40 deg C, 1 h, 2) THF, -78 deg C, 15 min
7: 96 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C
8: 85 percent / camphorsulfonic acid / CH2Cl2; methanol / 0.5 h / 0 - 25 °C
9: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 30 min, 2) CH2Cl2, -78 deg C -> 0 deg C, 30 min
10: 90 percent / NaClO2, isobutylene, NaH2PO4 / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 1 h / Ambient temperature
11: 73 percent / TBAF / tetrahydrofuran / 8 h / 25 °C
12: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-DMAP / 1) THF, 25 deg C, 15 min, 2) toluene, 25 deg C, 12 h
13: 91 percent / CF3CO2H / CH2Cl2 / 1) -20 deg C -> 0 deg C, 2) 0 deg C, 1 h
View Scheme
(S)-3-((tert-butyldimethylsilyl)oxy)-4,4-dimethyl-5-oxoheptanoic acid
187283-45-0

(S)-3-((tert-butyldimethylsilyl)oxy)-4,4-dimethyl-5-oxoheptanoic acid

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C
1.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C
2.1: pyridine / CH2Cl2 / 1 h / 0 °C
3.1: CH2Cl2 / 5 h / 20 °C
4.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
5.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
6.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
6.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
7.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
8.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: 2,4,6-Cl3C6H2COCl; TEA; DMAP / tetrahydrofuran; toluene / 1 h / 20 °C
2: 95 percent / HF / pyridine; CH2Cl2 / 20 °C
3: 92 percent / Zn; aq. NH4Cl / methanol / Heating
View Scheme
Multi-step reaction with 5 steps
1.1: titanium tetrachloride / dichloromethane / 0.08 h / -78 °C / Inert atmosphere
1.2: 1 h / -78 °C / Inert atmosphere
1.3: 3 h / -78 - 20 °C / Inert atmosphere
2.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C / Inert atmosphere
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere
4.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 0.67 h / 0 °C / Inert atmosphere
4.2: 20 °C / Inert atmosphere
5.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 h / 20 °C / Inert atmosphere
2.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / -78 °C / Inert atmosphere
2.2: 15 h / -12 °C / Inert atmosphere
3.1: 2,6-dimethylpyridine / dichloromethane / 5 h / -45 - 20 °C / Inert atmosphere
4.1: Hoveyda-Grubbs catalyst second generation / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
5.1: trifluoroacetic acid / dichloromethane / 2 h / -20 - 0 °C / Inert atmosphere
View Scheme
Multi-step reaction with 6 steps
1: phenyltrimethylammonium tribromide / tetrahydrofuran / 1.25 h / 0 - 20 °C
2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
3: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 2.5 h / 0 °C
4: triethylamine; sulfur trioxide pyridine complex; dimethyl sulfoxide / dichloromethane / 1 h / 0 °C / Inert atmosphere
5: lithium iodide; chromium dichloride / tetrahydrofuran / 3.33 h / 20 °C / Inert atmosphere
6: trifluoroacetic acid / dichloromethane / 1.5 h / 0 °C
View Scheme
(-)-(2R,3S,5Z)-2-(4-methoxybenzyloxy)-6,10-dimethylundeca-5,10-dien-3-ol
380605-86-7

(-)-(2R,3S,5Z)-2-(4-methoxybenzyloxy)-6,10-dimethylundeca-5,10-dien-3-ol

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1.1: 92 percent / DIPEA / CH2Cl2 / 6 h / 20 °C
2.1: 91 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 3 h / 20 °C
3.1: 85 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C
4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
4.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C
5.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C
5.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C
6.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C
7.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C
7.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C
8.1: pyridine / CH2Cl2 / 1 h / 0 °C
9.1: CH2Cl2 / 5 h / 20 °C
10.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
11.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
12.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
12.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
13.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
14.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme
Multi-step reaction with 10 steps
1: 92 percent / DIPEA; DCM / 0 °C
2: 88 percent / DDQ / H2O
3: 85 percent / DMSO; (COCl)2; DCM / triethylamine / -78 °C
4: 72 percent / n-BuLi / tetrahydrofuran
5: (i-PC)2BH; aq. sodium borate / tetrahydrofuran / 0.5 h
6: 92 percent / DMSO; (COCl)2; NEt3 / CH2Cl2 / -78 °C
7: 2,4,6-Cl3C6H2COCl; TEA; DMAP / tetrahydrofuran; toluene / 1 h / 20 °C
8: 95 percent / HF / pyridine; CH2Cl2 / 20 °C
9: 92 percent / Zn; aq. NH4Cl / methanol / Heating
View Scheme
(Z)-(S)-6,10-Dimethyl-3-(2-trimethylsilanyl-ethoxymethoxy)-undeca-5,10-dien-2-one
380605-89-0

(Z)-(S)-6,10-Dimethyl-3-(2-trimethylsilanyl-ethoxymethoxy)-undeca-5,10-dien-2-one

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
1.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C
2.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C
2.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C
3.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C
4.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C
4.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C
5.1: pyridine / CH2Cl2 / 1 h / 0 °C
6.1: CH2Cl2 / 5 h / 20 °C
7.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
8.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
9.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
9.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
10.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
11.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme
Multi-step reaction with 7 steps
1: 72 percent / n-BuLi / tetrahydrofuran
2: (i-PC)2BH; aq. sodium borate / tetrahydrofuran / 0.5 h
3: 92 percent / DMSO; (COCl)2; NEt3 / CH2Cl2 / -78 °C
4: 2,4,6-Cl3C6H2COCl; TEA; DMAP / tetrahydrofuran; toluene / 1 h / 20 °C
5: 95 percent / HF / pyridine; CH2Cl2 / 20 °C
6: 92 percent / Zn; aq. NH4Cl / methanol / Heating
View Scheme
(Z)-(2R,3S)-6,10-Dimethyl-3-(2-trimethylsilanyl-ethoxymethoxy)-undeca-5,10-dien-2-ol
380605-88-9

(Z)-(2R,3S)-6,10-Dimethyl-3-(2-trimethylsilanyl-ethoxymethoxy)-undeca-5,10-dien-2-ol

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: 85 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
2.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C
3.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C
3.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C
4.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C
5.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C
5.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C
6.1: pyridine / CH2Cl2 / 1 h / 0 °C
7.1: CH2Cl2 / 5 h / 20 °C
8.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
9.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
10.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
10.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
11.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
12.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme
Multi-step reaction with 8 steps
1: 85 percent / DMSO; (COCl)2; DCM / triethylamine / -78 °C
2: 72 percent / n-BuLi / tetrahydrofuran
3: (i-PC)2BH; aq. sodium borate / tetrahydrofuran / 0.5 h
4: 92 percent / DMSO; (COCl)2; NEt3 / CH2Cl2 / -78 °C
5: 2,4,6-Cl3C6H2COCl; TEA; DMAP / tetrahydrofuran; toluene / 1 h / 20 °C
6: 95 percent / HF / pyridine; CH2Cl2 / 20 °C
7: 92 percent / Zn; aq. NH4Cl / methanol / Heating
View Scheme
(2-{1-[1-(4-methoxy-benzyloxy)-ethyl]-4,8-dimethyl-nona-3,8-dienyloxymethoxy}-ethyl)-trimethyl-silane
380605-87-8

(2-{1-[1-(4-methoxy-benzyloxy)-ethyl]-4,8-dimethyl-nona-3,8-dienyloxymethoxy}-ethyl)-trimethyl-silane

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: 91 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 3 h / 20 °C
2.1: 85 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C
3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
3.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C
4.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C
4.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C
5.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C
6.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C
6.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C
7.1: pyridine / CH2Cl2 / 1 h / 0 °C
8.1: CH2Cl2 / 5 h / 20 °C
9.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
10.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
11.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
11.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
12.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
13.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme
Multi-step reaction with 9 steps
1: 88 percent / DDQ / H2O
2: 85 percent / DMSO; (COCl)2; DCM / triethylamine / -78 °C
3: 72 percent / n-BuLi / tetrahydrofuran
4: (i-PC)2BH; aq. sodium borate / tetrahydrofuran / 0.5 h
5: 92 percent / DMSO; (COCl)2; NEt3 / CH2Cl2 / -78 °C
6: 2,4,6-Cl3C6H2COCl; TEA; DMAP / tetrahydrofuran; toluene / 1 h / 20 °C
7: 95 percent / HF / pyridine; CH2Cl2 / 20 °C
8: 92 percent / Zn; aq. NH4Cl / methanol / Heating
View Scheme
2-methyl-4-[2,6,10-trimethyl-3-(2-trimethylsilanyl-ethoxymethoxy)-undeca-1,5,10-trienyl]-thiazole
380605-90-3

2-methyl-4-[2,6,10-trimethyl-3-(2-trimethylsilanyl-ethoxymethoxy)-undeca-1,5,10-trienyl]-thiazole

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C
1.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C
2.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C
3.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C
3.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C
4.1: pyridine / CH2Cl2 / 1 h / 0 °C
5.1: CH2Cl2 / 5 h / 20 °C
6.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
7.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
8.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
8.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
9.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
10.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1: (i-PC)2BH; aq. sodium borate / tetrahydrofuran / 0.5 h
2: 92 percent / DMSO; (COCl)2; NEt3 / CH2Cl2 / -78 °C
3: 2,4,6-Cl3C6H2COCl; TEA; DMAP / tetrahydrofuran; toluene / 1 h / 20 °C
4: 95 percent / HF / pyridine; CH2Cl2 / 20 °C
5: 92 percent / Zn; aq. NH4Cl / methanol / Heating
View Scheme
Carbonic acid (Z)-(4S,7R,8S,9S,16S)-4-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-2,6-dioxo-oxacyclohexadec-13-en-8-yl ester 2,2,2-trichloro-ethyl ester
380605-93-6

Carbonic acid (Z)-(4S,7R,8S,9S,16S)-4-(tert-butyl-dimethyl-silanyloxy)-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-2,6-dioxo-oxacyclohexadec-13-en-8-yl ester 2,2,2-trichloro-ethyl ester

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
2: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 95 percent / HF / pyridine; CH2Cl2 / 20 °C
2: 92 percent / Zn; aq. NH4Cl / methanol / Heating
View Scheme
(+)-(2S,6Z,9S,10E)-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)-9-(2-trimethylsilylethoxymethoxy)undeca-6,10-dienal
380605-84-5

(+)-(2S,6Z,9S,10E)-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)-9-(2-trimethylsilylethoxymethoxy)undeca-6,10-dienal

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C
1.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C
2.1: pyridine / CH2Cl2 / 1 h / 0 °C
3.1: CH2Cl2 / 5 h / 20 °C
4.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
5.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
6.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
6.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
7.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
8.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme
Multi-step reaction with 8 steps
1: 67 percent / Li(i-Pr)2N / -78 °C
2: 79 percent / Cl2CHCO2H
3: Dess-Martin periodinane
4: NaClO2
5: MgBr2; n-BuSH; K2CO3
6: 62 percent / 2,4,6-trichlorobenzoyl chloride; DMAP
7: 91 percent / CF3CO2H / CH2Cl2
View Scheme
Multi-step reaction with 4 steps
1: 2,4,6-Cl3C6H2COCl; TEA; DMAP / tetrahydrofuran; toluene / 1 h / 20 °C
2: 95 percent / HF / pyridine; CH2Cl2 / 20 °C
3: 92 percent / Zn; aq. NH4Cl / methanol / Heating
View Scheme
Multi-step reaction with 8 steps
1.1: lithium diisopropyl amide; n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - 40 °C
1.2: 0.03 h / -78 °C
2.1: 2,6-dimethylpyridine / dichloromethane / 6 h / 0 °C
3.1: dichloro-acetic acid / dichloromethane / 2 h / 20 °C
4.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C
5.1: sodium chlorite; sodium dihydrogenphosphate; 2,3-Dimethyl-2-butene / tetrahydrofuran; water; tert-butyl alcohol / 1 h / 20 °C
6.1: potassium carbonate; magnesium bromide ethyl etherate; n-butanethiol / diethyl ether / 2 h / 20 °C
7.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.75 h / 0 °C
7.2: 5 h / 75 °C
8.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
View Scheme
(2S,9S,6Z,10E)-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)-9-(2-trimethylsilylethoxy)methoxyundeca-6,10-dien-1-ol
380605-91-4

(2S,9S,6Z,10E)-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)-9-(2-trimethylsilylethoxy)methoxyundeca-6,10-dien-1-ol

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C
2.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C
2.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C
3.1: pyridine / CH2Cl2 / 1 h / 0 °C
4.1: CH2Cl2 / 5 h / 20 °C
5.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
6.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
7.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
7.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
8.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
9.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme
Multi-step reaction with 9 steps
1: Dess-Martin periodinane
2: 67 percent / Li(i-Pr)2N / -78 °C
3: 79 percent / Cl2CHCO2H
4: Dess-Martin periodinane
5: NaClO2
6: MgBr2; n-BuSH; K2CO3
7: 62 percent / 2,4,6-trichlorobenzoyl chloride; DMAP
8: 91 percent / CF3CO2H / CH2Cl2
View Scheme
Multi-step reaction with 5 steps
1: 92 percent / DMSO; (COCl)2; NEt3 / CH2Cl2 / -78 °C
2: 2,4,6-Cl3C6H2COCl; TEA; DMAP / tetrahydrofuran; toluene / 1 h / 20 °C
3: 95 percent / HF / pyridine; CH2Cl2 / 20 °C
4: 92 percent / Zn; aq. NH4Cl / methanol / Heating
View Scheme
Multi-step reaction with 9 steps
1.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C
2.1: lithium diisopropyl amide; n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - 40 °C
2.2: 0.03 h / -78 °C
3.1: 2,6-dimethylpyridine / dichloromethane / 6 h / 0 °C
4.1: dichloro-acetic acid / dichloromethane / 2 h / 20 °C
5.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C
6.1: sodium chlorite; sodium dihydrogenphosphate; 2,3-Dimethyl-2-butene / tetrahydrofuran; water; tert-butyl alcohol / 1 h / 20 °C
7.1: potassium carbonate; magnesium bromide ethyl etherate; n-butanethiol / diethyl ether / 2 h / 20 °C
8.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.75 h / 0 °C
8.2: 5 h / 75 °C
9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
View Scheme
(3S)-3-[((tert-butyl)dimethylsilyl)oxy]-1-[(1S,5R)-10,10-dimethyl-3,3-dioxido-3-thia-4-azatricyclo[5.2.1.01.5]dec-4-yl]-4,4-dimethylheptan-1,5-dione
250679-52-8

(3S)-3-[((tert-butyl)dimethylsilyl)oxy]-1-[(1S,5R)-10,10-dimethyl-3,3-dioxido-3-thia-4-azatricyclo[5.2.1.01.5]dec-4-yl]-4,4-dimethylheptan-1,5-dione

epothilone D
189453-10-9

epothilone D

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: 76 percent / lithium hydroxide; hydrogen peroxide / tetrahydrofuran; H2O / 4 h / 20 °C
2.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C
2.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C
3.1: pyridine / CH2Cl2 / 1 h / 0 °C
4.1: CH2Cl2 / 5 h / 20 °C
5.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
6.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
7.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
7.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
8.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
9.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1.1: lithium hydroxide monohydrate; dihydrogen peroxide / tetrahydrofuran; water / 24.5 h / 0 - 25 °C / Inert atmosphere
2.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 h / 20 °C / Inert atmosphere
3.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / -78 °C / Inert atmosphere
3.2: 15 h / -12 °C / Inert atmosphere
4.1: 2,6-dimethylpyridine / dichloromethane / 5 h / -45 - 20 °C / Inert atmosphere
5.1: Hoveyda-Grubbs catalyst second generation / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
6.1: trifluoroacetic acid / dichloromethane / 2 h / -20 - 0 °C / Inert atmosphere
View Scheme
epothilone D
189453-10-9

epothilone D

epothilone B
152044-54-7

epothilone B

Conditions
ConditionsYield
With 3,3-dimethyldioxirane In dichloromethane at -50℃;98%
With 3,3-dimethyldioxirane In dichloromethane; acetone at -78 - -50℃; for 2.5h; Epoxidation;97%
With 3,3-dimethyldioxirane In dichloromethane at -35℃;97%
t-butyldimethylsiyl triflate
69739-34-0

t-butyldimethylsiyl triflate

epothilone D
189453-10-9

epothilone D

(4S,7R,8S,9S,13Z,16S)-4,8-bis{[tert-butyl(dimethyl)silyl]oxy}-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]oxacyclohexadec-13-ene-2,6-dione
189453-35-8

(4S,7R,8S,9S,13Z,16S)-4,8-bis{[tert-butyl(dimethyl)silyl]oxy}-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]oxacyclohexadec-13-ene-2,6-dione

Conditions
ConditionsYield
With triethylamine In dichloromethane at -78℃;85%
With 2,6-dimethylpyridine In dichloromethane at 0℃; silylation;
epothilone D
189453-10-9

epothilone D

C27H42N2O5S

C27H42N2O5S

Conditions
ConditionsYield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; O-(2,4-dinitrophenyl)hydroxylamine at 25℃; for 4h; Inert atmosphere;70%
epothilone D
189453-10-9

epothilone D

A

epothilone B
152044-54-7

epothilone B

B

(1R,3S,7S,10R,11S,12S,16S)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione

(1R,3S,7S,10R,11S,12S,16S)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione

Conditions
ConditionsYield
With Oxone; 1,1,1-trifluoro-2-propanone; edetate disodium; sodium hydrogencarbonate In water; acetonitrile at 0℃;A 69%
B n/a
With 3,3-dimethyldioxirane In dichloromethane; acetone at -78 - -50℃;A 53%
B n/a
With 3-chloro-benzenecarboperoxoic acid In chloroform at -10 - 0℃; for 5h;A 30%
B n/a
epothilone D
189453-10-9

epothilone D

(1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4-oxa-17-azabicyclo[14.1.0]heptadecane-5,9-dione

(1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4-oxa-17-azabicyclo[14.1.0]heptadecane-5,9-dione

Conditions
ConditionsYield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; O-(2,4-dinitrophenyl)hydroxylamine In 2,2,2-trifluoroethanol at 25℃; for 4h; Inert atmosphere;66%
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; O-(2,4-dinitrophenyl)hydroxylamine In 2,2,2-trifluoroethanol at 25℃; for 4h;66%

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