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Dayang Chem (Hangzhou) Co.,Ltd.

DayangChem exported this product to many countries and regions at best price. If you are looking for the material's manufacturer or supplier in China, DayangChem is your best choice. Pls contact with us freely for getting detailed product spe

IXABEPILONE

Cas:219989-84-1

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

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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

High quality Ixabepilone Base supplier in China

Cas:219989-84-1

Min.Order:0 Metric Ton

Negotiable

Type:Manufacturers

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Hangzhou Think Chemical Co. Ltd

Ixabepilone CAS No.:219989-84-1 Name: Ixabepilone Synonyms: (1R,5S,6S,7R,10S,14S,16S)-6,10-Dihydroxy-1,5,7,9,9-pentamethyl-14-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-17-oxa-13-azabicyclo[14.1.0]heptadecane-8,12-

High purity Ixabepilone CAS No.:219989-84-1

Cas:219989-84-1

Min.Order:1 Kilogram

FOB Price: $2.0

Type:Other

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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% IXABEPILONE 219989-84-1 GMP Manufacturer

Cas:219989-84-1

Min.Order:1 Gram

FOB Price: $0.1

Type:Manufacturers

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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

Ixabepilone

Cas:219989-84-1

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

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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

IXABEPILONE

Cas:219989-84-1

Min.Order:1 Kilogram

FOB Price: $9.0 / 99.0

Type:Trading Company

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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 219989-84-1 with best quality

Cas:219989-84-1

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

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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

IXABEPILONE

Cas:219989-84-1

Min.Order:1 Kilogram

FOB Price: $5.0 / 10.0

Type:Trading Company

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Shijiazhuang Sdyano Fine Chemical Co., Ltd

1. Best prices with satisfied quality; 2. It's clients' right to choose the package's Courier (EMS, DHL, FedEx, UPS); 3.It's clients' right to choose the packing way for his produccts from many recent effective packing ways;

IXABEPILONE

Cas:219989-84-1

Min.Order:0 Metric Ton

Negotiable

Type:Trading Company

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HANWAYS CHEMPHARM CO.,LIMITED

Hanways chempharm is a specialized company concentrating on the R&D, production, marketing and technical service of APIs and pharmaceutical intermediates. The marketing department is located in Wuhan. We have two GMP facilities in Hu

Anti-tumor powder 99% Ixabepilone/Bms 247550-1/Ixempra CAS 219989-84-1

Cas:219989-84-1

Min.Order:10 Gram

FOB Price: $100.0 / 150.0

Type:Trading Company

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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

IXABEPILONE CAS: 219989-84-1 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

IXABEPILONE CAS: 219989-84-1

Cas:219989-84-1

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

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

IXABEPILONE CAS 219989-84-1

Cas:219989-84-1

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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Guangdong Juda Chemical Industrial Co.,Limited

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 etc. 3) OEM/ODM Available;

Ixabepilone CAS 219989-84-1

Cas:219989-84-1

Min.Order:1 Gram

Negotiable

Type:Trading Company

inquiry

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

Triumph International Development Limilted

Appearance:white or light yellow crystalline powder Storage:Store in a cool,dry place and keep away from direct strong light Package:As customer request Application:Used for research and industrial manufacture. Transportation:By

IXABEPILONE 219989-84-1

Cas:219989-84-1

Min.Order:0 Metric Ton

Negotiable

Type:Lab/Research institutions

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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

Ixabepilone

Cas:219989-84-1

Min.Order:1 Kilogram

FOB Price: $1.0 / 100000.0

Type:Lab/Research institutions

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Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd

Specification:USP/EP Month production ablity:50kg/Month Low price& High quality Manufacturer Appearance:white powder Storage:Room Temperature Application:219989-84-1

Ixabepilone

Cas:219989-84-1

Min.Order:0 Metric Ton

Negotiable

Type:Other

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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-

BMS-247550 Ixabepilone 219989-84-1

Cas:219989-84-1

Min.Order:500 Milligram

Negotiable

Type:Lab/Research institutions

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Hangzhou Keyingchem Co.,Ltd

Hangzhou KeyingChem Co., Ltd. exported this product to many countries and regions at best price. If you are looking for the material’s manufacturer or supplier in China, KeyingChem is your best choice. Pls contact with us freely for getting det

Ixabepilone

Cas:219989-84-1

Min.Order:0 Metric Ton

Negotiable

Type:Lab/Research institutions

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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

Ixabepilone

Cas:219989-84-1

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou Fonlynn Health Technology Co., Ltd.

Packing: According to customer requirements Delivery time: In stock or depands Port of shipment: Ningbo/Shanghai/Qingdao OEM/ODM:Welcome Sample:We can offer our existing samples at once Transportation:Express/Sea/Air Port:Ningbo/Shanghai/Qingd

Ixabepilone

Cas:219989-84-1

Min.Order:0

Negotiable

Type:Trading Company

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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

High quality Ixabepilone Base

Cas:219989-84-1

Min.Order:10 Gram

FOB Price: $100.0

Type:Lab/Research institutions

inquiry

Hangzhou Lingrui Chemical Co.,Ltd.

High Quality Ixabepilone 219989-84-1 in stock fast delivery good supplierAppearance:Powder Storage:Dry and ventilated Package:according to customers' requirements Application:APIs Transportation:By air(EMS or EUB or FedEx or TNT ect...) or by sea(FOB

High Quality Ixabepilone 219989-84-1 in stock fast delivery good supplier

Cas:219989-84-1

Min.Order:1 Gram

Negotiable

Type:Other

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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

IXABEPILONE

Cas:219989-84-1

Min.Order:10 Gram

Negotiable

Type:Lab/Research institutions

inquiry

HANGZHOU YUNUO CHEMICAL CO.,LTD

Superior quality, moderate price & quick delivery. Appearance:White solid Storage:Stored in cool, dry and ventilation place; Away from fire and heat Package:1g/bag, 10g/bag, 100g/bag, 500g/bag or as per your request Application:Used as Pharmace

Zibo Dorne chemical technology co. LTD

Product Details Grade: pharmaceutical grade Purity:99%+ ProductionCapacity: 1000 Kilogram/Month Scope of use: For scientific research only(The product must be used legally) Our Advantage 1. Best quality with competitive price. 2. Quick shipping,

Aza-epothilone B

Cas:219989-84-1

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Siwei Development Group Ltd.

Product name: Ixabepilone CAS No.:219989-84-1 Molecule Formula:C27H42N2O5S Molecule Weight:506.70 Purity: 99.0% Package: 25kg/drum Description:White or light yellow crystalline powder Manufacture Standards:Enterprise Standard

Best Quality Ixabepilone

Cas:219989-84-1

Min.Order:1 Kilogram

Negotiable

Type:Trading Company

inquiry

Jiangsu Qianyu Molecular Technology Co., LTD.

Our Advantages A. International Top level TechnologyOur company owned biomedicine experts are famous at home and abroad with rich experience in research and development in the field of efficient chiral functional molecules research and development an

Best OfferIXABEPILONE

Cas:219989-84-1

Min.Order:0

Negotiable

Type:Trading Company

inquiry

Synthetic route

[4S-[4R*,7S*,8R*,9R*,15R*(E)]]-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-1-aza-13(Z)-cyclohexadecene-2,6-dione
219989-87-4

[4S-[4R*,7S*,8R*,9R*,15R*(E)]]-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-1-aza-13(Z)-cyclohexadecene-2,6-dione

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
With DMDO In dichloromethane at -78 - -50℃; for 1h;69%
With 3,3-dimethyldioxirane In dichloromethane; acetone at -78 - -50℃; for 1.5h; Inert atmosphere;42.8%
With 3-chloro-benzenecarboperoxoic acid In chloroform at -20 - -15℃; for 4h; Inert atmosphere;0.31 g
(3S,6R,7S,8S,12R,13S,15S)-15-amino-12,13-epoxy-4,4,6,8,12,16-hexamethyl-3,7-dihydroxy-17-(2-methyl-4-thiazolyl)-5-oxo-16-heptadecenoic acid

(3S,6R,7S,8S,12R,13S,15S)-15-amino-12,13-epoxy-4,4,6,8,12,16-hexamethyl-3,7-dihydroxy-17-(2-methyl-4-thiazolyl)-5-oxo-16-heptadecenoic acid

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
With diphenyl phosphoryl azide; sodium hydrogencarbonate In N,N-dimethyl-formamide at 0 - 4℃; for 24h; Inert atmosphere;40%
(3S,6R,7S,8S)-11-((2R,3S)-3-((S,E)-2-amino-3-methyl-4-(2-methylthiazol-4-yl)but-3-enyl)-2-methyloxiran-2-yl)-3,7-dihydroxy-4,4,6,8-tetramethyl-5-oxoundecanoic acid
219990-25-7

(3S,6R,7S,8S)-11-((2R,3S)-3-((S,E)-2-amino-3-methyl-4-(2-methylthiazol-4-yl)but-3-enyl)-2-methyloxiran-2-yl)-3,7-dihydroxy-4,4,6,8-tetramethyl-5-oxoundecanoic acid

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
With diphenyl-phosphinic acid; sodium hydrogencarbonate In N,N-dimethyl-formamide at 4℃; for 24h;43%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide; acetonitrile at 0 - 30℃; for 12h; Inert atmosphere;3.2 g
C29H47N3O7S
1417803-30-5

C29H47N3O7S

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
With diphenyl phosphoryl azide; sodium hydrogencarbonate In N,N-dimethyl-formamide at 0℃; for 24h; Inert atmosphere;
(3S,6R,7S,8S)-11-((2R,3S)-3-((S,E)-2-azido-3-methyl-4-(2-methylthiazol-4-yl)but-3-enyl)-2-methyloxiran-2-yl)-3,7-dihydroxy-4,4,6,8-tetramethyl-5-oxoundecanoic acid
219990-23-5

(3S,6R,7S,8S)-11-((2R,3S)-3-((S,E)-2-azido-3-methyl-4-(2-methylthiazol-4-yl)but-3-enyl)-2-methyloxiran-2-yl)-3,7-dihydroxy-4,4,6,8-tetramethyl-5-oxoundecanoic acid

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 71 percent / PMe3; H2O / tetrahydrofuran; toluene / 2 h / 25 °C
2: 43 percent / DPPA; NaHCO3 / dimethylformamide / 24 h / 4 °C
View Scheme
Multi-step reaction with 2 steps
1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere
2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere
View Scheme
epothilone B
152044-54-7

epothilone B

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere
1.2: 1 h / 45 °C
2.1: triphenylphosphine / tetrahydrofuran / 14 h / 45 °C / Inert atmosphere
2.2: 4 h / 45 °C
3.1: sodium hydrogencarbonate; diphenyl phosphoryl azide / N,N-dimethyl-formamide / 24 h / 0 - 4 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere
2: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere
3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere
View Scheme
(Z)-(6R,7S,8S)-3-Methoxy-4,4,6,8-tetramethyl-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-undeca-2,10-dienoic acid tert-butyl ester
224580-49-8

(Z)-(6R,7S,8S)-3-Methoxy-4,4,6,8-tetramethyl-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-undeca-2,10-dienoic acid tert-butyl ester

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: tetrahydrofuran / 1 h / 25 °C
2: 70 percent / Pd(dppf)Cl2*CH2Cl2; AsPh3; Cs2CO3 / dimethylformamide; H2O; tetrahydrofuran / 2 h
3: tetrahydrofuran / 19 h / 40 °C
4: 3.9 g / H2O / tetrahydrofuran / 4 h / 65 °C
5: 70 percent / Et3N / acetonitrile / 16 h / 20 °C
6: 82 percent / p-TsOH / acetone / 22 h / 20 °C
7: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr
8: TFA / CH2Cl2 / 2 h / 20 °C
9: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C
10: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C
11: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C
View Scheme
(5R)-5-hydroxy-2-iodo-6-methyl-7-(2-methylthiazol-4-yl)-2,6-heptadiene
277749-45-8

(5R)-5-hydroxy-2-iodo-6-methyl-7-(2-methylthiazol-4-yl)-2,6-heptadiene

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 85 percent / diphenylphosphoryl azide; DBU / toluene / 2 h / 2 - 25 °C
2: 70 percent / Pd(dppf)Cl2*CH2Cl2; AsPh3; Cs2CO3 / dimethylformamide; H2O; tetrahydrofuran / 2 h
3: tetrahydrofuran / 19 h / 40 °C
4: 3.9 g / H2O / tetrahydrofuran / 4 h / 65 °C
5: 70 percent / Et3N / acetonitrile / 16 h / 20 °C
6: 82 percent / p-TsOH / acetone / 22 h / 20 °C
7: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr
8: TFA / CH2Cl2 / 2 h / 20 °C
9: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C
10: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C
11: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C
View Scheme
(5S)-5-azido-2-iodo-6-methyl-7-(2-methylthiazol-4-yl)-2,6-heptadiene
277749-36-7

(5S)-5-azido-2-iodo-6-methyl-7-(2-methylthiazol-4-yl)-2,6-heptadiene

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 70 percent / Pd(dppf)Cl2*CH2Cl2; AsPh3; Cs2CO3 / dimethylformamide; H2O; tetrahydrofuran / 2 h
2: tetrahydrofuran / 19 h / 40 °C
3: 3.9 g / H2O / tetrahydrofuran / 4 h / 65 °C
4: 70 percent / Et3N / acetonitrile / 16 h / 20 °C
5: 82 percent / p-TsOH / acetone / 22 h / 20 °C
6: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr
7: TFA / CH2Cl2 / 2 h / 20 °C
8: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C
9: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C
10: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C
View Scheme
4-((1E,5Z)-(R)-6-Iodo-2-methyl-3-triethylsilanyloxy-hepta-1,5-dienyl)-2-methyl-thiazole

4-((1E,5Z)-(R)-6-Iodo-2-methyl-3-triethylsilanyloxy-hepta-1,5-dienyl)-2-methyl-thiazole

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: 99 percent / aq. AcOH / tetrahydrofuran / 8 h / 20 °C
2: 85 percent / diphenylphosphoryl azide; DBU / toluene / 2 h / 2 - 25 °C
3: 70 percent / Pd(dppf)Cl2*CH2Cl2; AsPh3; Cs2CO3 / dimethylformamide; H2O; tetrahydrofuran / 2 h
4: tetrahydrofuran / 19 h / 40 °C
5: 3.9 g / H2O / tetrahydrofuran / 4 h / 65 °C
6: 70 percent / Et3N / acetonitrile / 16 h / 20 °C
7: 82 percent / p-TsOH / acetone / 22 h / 20 °C
8: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr
9: TFA / CH2Cl2 / 2 h / 20 °C
10: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C
11: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C
12: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C
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-azacyclohexadec-13-en-8-yl ester 2,2,2-trichloro-ethyl ester
277749-43-6

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-azacyclohexadec-13-en-8-yl ester 2,2,2-trichloro-ethyl ester

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C
2: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C
View Scheme
(12Z,16E)-(3S,6R,7S,8S,15S)-15-Amino-3-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
350042-12-5

(12Z,16E)-(3S,6R,7S,8S,15S)-15-Amino-3-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

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C
2: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C
3: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C
View Scheme
(2Z,12Z,16E)-(6R,7S,8S,15S)-15-Amino-3-methoxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-heptadeca-2,12,16-trienoic acid tert-butyl ester
350042-19-2

(2Z,12Z,16E)-(6R,7S,8S,15S)-15-Amino-3-methoxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-heptadeca-2,12,16-trienoic acid tert-butyl ester

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 70 percent / Et3N / acetonitrile / 16 h / 20 °C
2: 82 percent / p-TsOH / acetone / 22 h / 20 °C
3: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr
4: TFA / CH2Cl2 / 2 h / 20 °C
5: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C
6: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C
7: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C
View Scheme
(2Z,12Z,16E)-(6R,7S,8S,15S)-15-Azido-3-methoxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-heptadeca-2,12,16-trienoic acid tert-butyl ester
350042-09-0

(2Z,12Z,16E)-(6R,7S,8S,15S)-15-Azido-3-methoxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-heptadeca-2,12,16-trienoic acid tert-butyl ester

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: tetrahydrofuran / 19 h / 40 °C
2: 3.9 g / H2O / tetrahydrofuran / 4 h / 65 °C
3: 70 percent / Et3N / acetonitrile / 16 h / 20 °C
4: 82 percent / p-TsOH / acetone / 22 h / 20 °C
5: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr
6: TFA / CH2Cl2 / 2 h / 20 °C
7: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C
8: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C
9: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C
View Scheme
(12Z,16E)-(6R,7S,8S,15S)-15-tert-Butoxycarbonylamino-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-3,5-dioxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-heptadeca-12,16-dienoic acid tert-butyl ester
277749-41-4

(12Z,16E)-(6R,7S,8S,15S)-15-tert-Butoxycarbonylamino-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-3,5-dioxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-heptadeca-12,16-dienoic acid tert-butyl ester

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr
2: TFA / CH2Cl2 / 2 h / 20 °C
3: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C
4: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C
5: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C
View Scheme
(2Z,12Z,16E)-(6R,7S,8S,15S)-15-tert-Butoxycarbonylamino-3-methoxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-heptadeca-2,12,16-trienoic acid tert-butyl ester
350042-11-4

(2Z,12Z,16E)-(6R,7S,8S,15S)-15-tert-Butoxycarbonylamino-3-methoxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-heptadeca-2,12,16-trienoic acid tert-butyl ester

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 82 percent / p-TsOH / acetone / 22 h / 20 °C
2: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr
3: TFA / CH2Cl2 / 2 h / 20 °C
4: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C
5: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C
6: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C
View Scheme
(12Z,16E)-(3S,6R,7S,8S,15S)-15-tert-Butoxycarbonylamino-3-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 tert-butyl ester
277749-42-5

(12Z,16E)-(3S,6R,7S,8S,15S)-15-tert-Butoxycarbonylamino-3-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 tert-butyl ester

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: TFA / CH2Cl2 / 2 h / 20 °C
2: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C
3: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C
4: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C
View Scheme
(Z)-(6R,7S,8S)-11-(9-Bora-bicyclo[3.3.1]non-9-yl)-3-methoxy-4,4,6,8-tetramethyl-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-undec-2-enoic acid tert-butyl ester

(Z)-(6R,7S,8S)-11-(9-Bora-bicyclo[3.3.1]non-9-yl)-3-methoxy-4,4,6,8-tetramethyl-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-undec-2-enoic acid tert-butyl ester

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 70 percent / Pd(dppf)Cl2*CH2Cl2; AsPh3; Cs2CO3 / dimethylformamide; H2O; tetrahydrofuran / 2 h
2: tetrahydrofuran / 19 h / 40 °C
3: 3.9 g / H2O / tetrahydrofuran / 4 h / 65 °C
4: 70 percent / Et3N / acetonitrile / 16 h / 20 °C
5: 82 percent / p-TsOH / acetone / 22 h / 20 °C
6: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr
7: TFA / CH2Cl2 / 2 h / 20 °C
8: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C
9: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C
10: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C
View Scheme
C35H51Cl3N2O7SP(C6H5)3

C35H51Cl3N2O7SP(C6H5)3

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 3.9 g / H2O / tetrahydrofuran / 4 h / 65 °C
2: 70 percent / Et3N / acetonitrile / 16 h / 20 °C
3: 82 percent / p-TsOH / acetone / 22 h / 20 °C
4: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr
5: TFA / CH2Cl2 / 2 h / 20 °C
6: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C
7: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C
8: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C
View Scheme
(E)-2-methyl-3-(2-methylthiazol-4-yl)acrylaldehyde
184246-38-6

(E)-2-methyl-3-(2-methylthiazol-4-yl)acrylaldehyde

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere
2.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere
2.2: -50 - 20 °C
3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C
4.1: triethylamine / tetrahydrofuran / 20 °C
5.1: 4-methylmorpholine N-oxide; potassium osmate monohydrate / water; acetone / 3 h / 30 °C
5.2: 0.5 h / 30 °C
5.3: 1 h / 30 °C
6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere
6.2: 0.5 h / -60 - -50 °C
7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
7.2: 0.5 h
7.3: 50 °C
8.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C
9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C
11.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 11 steps
1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere
2.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere
2.2: -50 - 20 °C
3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C
4.1: triethylamine / tetrahydrofuran / 20 °C
5.1: 4-methylmorpholine N-oxide; potassium osmate monohydrate / water; acetone / 3 h / 30 °C
5.2: 0.5 h / 30 °C
5.3: 1 h / 30 °C
6.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere
6.2: 0.42 h / -20 °C
6.3: 1 h / -20 - 10 °C
7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
7.2: 0.5 h
7.3: 50 °C
8.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C
9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C
11.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 11 steps
1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere
2.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere
2.2: 6 h / -78 °C / Inert atmosphere
3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C
4.1: triethylamine / tetrahydrofuran / 20 °C
5.1: 4-methylmorpholine N-oxide; potassium osmate monohydrate / water; acetone / 3 h / 30 °C
5.2: 0.5 h / 30 °C
5.3: 1 h / 30 °C
6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere
6.2: 0.5 h / -60 - -50 °C
7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
7.2: 0.5 h
7.3: 50 °C
8.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C
9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C
11.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
C15H24N2OS2

C15H24N2OS2

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C
2.1: triethylamine / tetrahydrofuran / 20 °C
3.1: 4-methylmorpholine N-oxide; potassium osmate monohydrate / water; acetone / 3 h / 30 °C
3.2: 0.5 h / 30 °C
3.3: 1 h / 30 °C
4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere
4.2: 0.5 h / -60 - -50 °C
5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
5.2: 0.5 h
5.3: 50 °C
6.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
7.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C
8.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C
9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 10 steps
1.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C
2.1: triethylamine / tetrahydrofuran / 20 °C
3.1: 4-methylmorpholine N-oxide; potassium osmate monohydrate / water; acetone / 3 h / 30 °C
3.2: 0.5 h / 30 °C
3.3: 1 h / 30 °C
4.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere
4.2: 0.42 h / -20 °C
4.3: 1 h / -20 - 10 °C
5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
5.2: 0.5 h
5.3: 50 °C
6.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
7.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C
8.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C
9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 10 steps
1.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C
2.1: triethylamine / tetrahydrofuran / 20 °C
3.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C
4.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C
5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere
5.2: 0.5 h / -60 - -50 °C
6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
6.2: 0.5 h
6.3: 50 °C
7.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C
8.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
9.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C
10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
(S)-4-[3-[N-[(tert-butyloxy)carbonyl]amino]-2-methyl-1(E),5-hexadienyl]-2-methylthiazole
219990-13-3

(S)-4-[3-[N-[(tert-butyloxy)carbonyl]amino]-2-methyl-1(E),5-hexadienyl]-2-methylthiazole

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 4-methylmorpholine N-oxide; potassium osmate monohydrate / water; acetone / 3 h / 30 °C
1.2: 0.5 h / 30 °C
1.3: 1 h / 30 °C
2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere
2.2: 0.5 h / -60 - -50 °C
3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
3.2: 0.5 h
3.3: 50 °C
4.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C
5.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
6.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C
7.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 7 steps
1.1: 4-methylmorpholine N-oxide; potassium osmate monohydrate / water; acetone / 3 h / 30 °C
1.2: 0.5 h / 30 °C
1.3: 1 h / 30 °C
2.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere
2.2: 0.42 h / -20 °C
2.3: 1 h / -20 - 10 °C
3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
3.2: 0.5 h
3.3: 50 °C
4.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C
5.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
6.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C
7.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 8 steps
1.1: 4-methylmorpholine N-oxide; potassium osmate monohydrate / water; acetone / 3 h / 30 °C
1.2: 0.5 h / 30 °C
1.3: 1 h / 30 °C
2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere
2.2: 0.5 h / -60 - -50 °C
3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
3.2: 0.5 h
3.3: 50 °C
4.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
5.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C
6.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C
7.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
8.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
C16H26N2O4S

C16H26N2O4S

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C
2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere
2.2: 0.5 h / -60 - -50 °C
3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
3.2: 0.5 h
3.3: 50 °C
4.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C
5.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
6.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C
7.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 7 steps
1.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C
2.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere
2.2: 0.42 h / -20 °C
2.3: 1 h / -20 - 10 °C
3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
3.2: 0.5 h
3.3: 50 °C
4.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C
5.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
6.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C
7.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 8 steps
1.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C
2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere
2.2: 0.5 h / -60 - -50 °C
3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
3.2: 0.5 h
3.3: 50 °C
4.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
5.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C
6.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C
7.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
8.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
C15H22N2O3S

C15H22N2O3S

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere
1.2: 0.5 h / -60 - -50 °C
2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
2.2: 0.5 h
2.3: 50 °C
3.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C
4.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
5.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C
6.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 6 steps
1.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere
1.2: 0.42 h / -20 °C
1.3: 1 h / -20 - 10 °C
2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
2.2: 0.5 h
2.3: 50 °C
3.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C
4.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
5.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C
6.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 7 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere
1.2: 0.5 h / -60 - -50 °C
2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
2.2: 0.5 h
2.3: 50 °C
3.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
4.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C
5.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C
6.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
7.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
C12H18N2OS2

C12H18N2OS2

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere
1.2: -50 - 20 °C
2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C
3.1: triethylamine / tetrahydrofuran / 20 °C
4.1: 4-methylmorpholine N-oxide; potassium osmate monohydrate / water; acetone / 3 h / 30 °C
4.2: 0.5 h / 30 °C
4.3: 1 h / 30 °C
5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere
5.2: 0.5 h / -60 - -50 °C
6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
6.2: 0.5 h
6.3: 50 °C
7.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C
8.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
9.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C
10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 10 steps
1.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere
1.2: -50 - 20 °C
2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C
3.1: triethylamine / tetrahydrofuran / 20 °C
4.1: 4-methylmorpholine N-oxide; potassium osmate monohydrate / water; acetone / 3 h / 30 °C
4.2: 0.5 h / 30 °C
4.3: 1 h / 30 °C
5.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere
5.2: 0.42 h / -20 °C
5.3: 1 h / -20 - 10 °C
6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
6.2: 0.5 h
6.3: 50 °C
7.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C
8.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
9.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C
10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 10 steps
1.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere
1.2: 6 h / -78 °C / Inert atmosphere
2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C
3.1: triethylamine / tetrahydrofuran / 20 °C
4.1: 4-methylmorpholine N-oxide; potassium osmate monohydrate / water; acetone / 3 h / 30 °C
4.2: 0.5 h / 30 °C
4.3: 1 h / 30 °C
5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere
5.2: 0.5 h / -60 - -50 °C
6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
6.2: 0.5 h
6.3: 50 °C
7.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C
8.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
9.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C
10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
(S)-4-(3-amino-2-methyl-1(E),5-hexadienyl)-2-methylthiazole
219990-14-4

(S)-4-(3-amino-2-methyl-1(E),5-hexadienyl)-2-methylthiazole

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: triethylamine / tetrahydrofuran / 20 °C
2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C
2.2: 20 °C
3.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; water; tert-butyl alcohol / 18 h / 0 - 20 °C
4.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C
5.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere
5.2: 0.08 h / -20 °C
5.3: 1 h / -20 - 10 °C
6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 1 h / 20 °C
6.2: 0.5 h
6.3: 0.5 h / 20 °C
7.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
8.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C
9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 10 steps
1.1: triethylamine / tetrahydrofuran / 20 °C
2.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C
3.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C
4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere
4.2: 0.5 h / -60 - -50 °C
5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
5.2: 0.5 h
5.3: 50 °C
6.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
7.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C
8.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C
9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 10 steps
1.1: triethylamine / tetrahydrofuran / 20 °C
2.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C
3.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C
4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere
4.2: 0.5 h / -60 - -50 °C
5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
5.2: 0.5 h
5.3: 50 °C
6.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C
7.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C
8.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C
9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
(-)-(3S)-3,5-bis(tert-butyldimethylsilyloxy)-pentan-2-one
188899-12-9

(-)-(3S)-3,5-bis(tert-butyldimethylsilyloxy)-pentan-2-one

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 18 steps
1.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere
1.2: 14 h / -75 - 30 °C
2.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C
3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere
4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere
4.2: 0.75 h / -75 - -35 °C / Inert atmosphere
5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere
5.2: 2 h / 25 - 30 °C / Inert atmosphere
6.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere
7.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere
7.2: 1 h / -78 °C
8.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere
9.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
10.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
11.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; tert-butyl alcohol / 2 h / 0 - 30 °C
12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere
13.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
13.2: 3 h / 0 - 30 °C / Inert atmosphere
14.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere
15.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere
16.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere
17.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere
18.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere
View Scheme
Multi-step reaction with 18 steps
1.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere
1.2: 14 h / -75 - 30 °C
2.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C
3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere
4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere
4.2: 0.75 h / -75 - -35 °C / Inert atmosphere
5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere
5.2: 2 h / 25 - 30 °C / Inert atmosphere
6.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere
7.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere
7.2: 1 h / -78 °C
8.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere
9.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
10.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
11.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; tert-butyl alcohol / 2 h / 0 - 30 °C
12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere
13.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
13.2: 3 h / 0 - 30 °C / Inert atmosphere
14.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere
15.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere
16.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere
17.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere
18.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere
View Scheme
Multi-step reaction with 19 steps
1.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere
1.2: 14 h / -75 - 30 °C
2.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C
3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere
4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere
4.2: 0.75 h / -75 - -35 °C / Inert atmosphere
5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere
5.2: 2 h / 25 - 30 °C / Inert atmosphere
6.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
7.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
8.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere
8.2: 1 h / -78 °C
9.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere
10.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
11.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
12.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; tert-butyl alcohol / 2 h / 0 - 30 °C
13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere
14.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
14.2: 3 h / 0 - 30 °C / Inert atmosphere
15.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere
16.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere
17.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere
18.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere
19.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere
View Scheme
(R)-3,5-dihydroxypentanenitrile

(R)-3,5-dihydroxypentanenitrile

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 24 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 7 h / 25 - 70 °C
2.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere
3.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C
4.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C
5.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere
6.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave
6.2: 2 h / 70 - 75 °C
7.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere
7.2: 14 h / -75 - 30 °C
8.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C
9.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere
10.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere
10.2: 0.75 h / -75 - -35 °C / Inert atmosphere
11.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere
11.2: 2 h / 25 - 30 °C / Inert atmosphere
12.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere
13.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere
13.2: 1 h / -78 °C
14.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere
15.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
16.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
17.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; tert-butyl alcohol / 2 h / 0 - 30 °C
18.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere
19.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
19.2: 3 h / 0 - 30 °C / Inert atmosphere
20.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere
21.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere
22.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere
23.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere
24.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere
View Scheme
Multi-step reaction with 24 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 7 h / 25 - 70 °C
2.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere
3.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C
4.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C
5.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere
6.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave
6.2: 2 h / 70 - 75 °C
7.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere
7.2: 14 h / -75 - 30 °C
8.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C
9.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere
10.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere
10.2: 0.75 h / -75 - -35 °C / Inert atmosphere
11.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere
11.2: 2 h / 25 - 30 °C / Inert atmosphere
12.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere
13.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere
13.2: 1 h / -78 °C
14.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere
15.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
16.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
17.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; tert-butyl alcohol / 2 h / 0 - 30 °C
18.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere
19.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
19.2: 3 h / 0 - 30 °C / Inert atmosphere
20.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere
21.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere
22.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere
23.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere
24.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere
View Scheme
Multi-step reaction with 25 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 7 h / 25 - 70 °C
2.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere
3.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C
4.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C
5.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere
6.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave
6.2: 2 h / 70 - 75 °C
7.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere
7.2: 14 h / -75 - 30 °C
8.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C
9.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere
10.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere
10.2: 0.75 h / -75 - -35 °C / Inert atmosphere
11.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere
11.2: 2 h / 25 - 30 °C / Inert atmosphere
12.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
13.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
14.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere
14.2: 1 h / -78 °C
15.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere
16.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
17.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
18.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; tert-butyl alcohol / 2 h / 0 - 30 °C
19.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere
20.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
20.2: 3 h / 0 - 30 °C / Inert atmosphere
21.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere
22.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere
23.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere
24.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere
25.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere
View Scheme
(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 25 steps
1.1: sodium tetrahydroborate; methanol / 8.25 h / 0 - 30 °C
2.1: 1H-imidazole / N,N-dimethyl-formamide / 7 h / 25 - 70 °C
3.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere
4.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C
5.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C
6.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere
7.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave
7.2: 2 h / 70 - 75 °C
8.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere
8.2: 14 h / -75 - 30 °C
9.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C
10.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere
11.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere
11.2: 0.75 h / -75 - -35 °C / Inert atmosphere
12.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere
12.2: 2 h / 25 - 30 °C / Inert atmosphere
13.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere
14.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere
14.2: 1 h / -78 °C
15.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere
16.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
17.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
18.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; tert-butyl alcohol / 2 h / 0 - 30 °C
19.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere
20.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
20.2: 3 h / 0 - 30 °C / Inert atmosphere
21.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere
22.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere
23.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere
24.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere
25.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere
View Scheme
Multi-step reaction with 25 steps
1.1: sodium tetrahydroborate; methanol / 8.25 h / 0 - 30 °C
2.1: 1H-imidazole / N,N-dimethyl-formamide / 7 h / 25 - 70 °C
3.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere
4.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C
5.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C
6.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere
7.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave
7.2: 2 h / 70 - 75 °C
8.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere
8.2: 14 h / -75 - 30 °C
9.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C
10.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere
11.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere
11.2: 0.75 h / -75 - -35 °C / Inert atmosphere
12.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere
12.2: 2 h / 25 - 30 °C / Inert atmosphere
13.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere
14.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere
14.2: 1 h / -78 °C
15.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere
16.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
17.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
18.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; tert-butyl alcohol / 2 h / 0 - 30 °C
19.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere
20.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
20.2: 3 h / 0 - 30 °C / Inert atmosphere
21.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere
22.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere
23.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere
24.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere
25.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere
View Scheme
Multi-step reaction with 26 steps
1.1: sodium tetrahydroborate; methanol / 8.25 h / 0 - 30 °C
2.1: 1H-imidazole / N,N-dimethyl-formamide / 7 h / 25 - 70 °C
3.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere
4.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C
5.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C
6.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere
7.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave
7.2: 2 h / 70 - 75 °C
8.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere
8.2: 14 h / -75 - 30 °C
9.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C
10.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere
11.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere
11.2: 0.75 h / -75 - -35 °C / Inert atmosphere
12.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere
12.2: 2 h / 25 - 30 °C / Inert atmosphere
13.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
14.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
15.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere
15.2: 1 h / -78 °C
16.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere
17.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
18.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
19.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; tert-butyl alcohol / 2 h / 0 - 30 °C
20.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere
21.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
21.2: 3 h / 0 - 30 °C / Inert atmosphere
22.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere
23.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere
24.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere
25.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere
26.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere
View Scheme
(R)-3,5-bis(tert-butyldimethylsilyloxy)pentanenitrile

(R)-3,5-bis(tert-butyldimethylsilyloxy)pentanenitrile

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 23 steps
1.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere
2.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C
3.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C
4.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere
5.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave
5.2: 2 h / 70 - 75 °C
6.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere
6.2: 14 h / -75 - 30 °C
7.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C
8.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere
9.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere
9.2: 0.75 h / -75 - -35 °C / Inert atmosphere
10.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere
10.2: 2 h / 25 - 30 °C / Inert atmosphere
11.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere
12.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere
12.2: 1 h / -78 °C
13.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere
14.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
15.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
16.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; tert-butyl alcohol / 2 h / 0 - 30 °C
17.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere
18.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
18.2: 3 h / 0 - 30 °C / Inert atmosphere
19.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere
20.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere
21.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere
22.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere
23.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere
View Scheme
Multi-step reaction with 23 steps
1.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere
2.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C
3.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C
4.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere
5.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave
5.2: 2 h / 70 - 75 °C
6.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere
6.2: 14 h / -75 - 30 °C
7.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C
8.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere
9.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere
9.2: 0.75 h / -75 - -35 °C / Inert atmosphere
10.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere
10.2: 2 h / 25 - 30 °C / Inert atmosphere
11.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere
12.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere
12.2: 1 h / -78 °C
13.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere
14.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
15.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
16.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; tert-butyl alcohol / 2 h / 0 - 30 °C
17.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere
18.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
18.2: 3 h / 0 - 30 °C / Inert atmosphere
19.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere
20.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere
21.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere
22.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere
23.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere
View Scheme
Multi-step reaction with 24 steps
1.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere
2.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C
3.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C
4.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere
5.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave
5.2: 2 h / 70 - 75 °C
6.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere
6.2: 14 h / -75 - 30 °C
7.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C
8.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere
9.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere
9.2: 0.75 h / -75 - -35 °C / Inert atmosphere
10.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere
10.2: 2 h / 25 - 30 °C / Inert atmosphere
11.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
12.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
13.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere
13.2: 1 h / -78 °C
14.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere
15.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
16.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
17.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; tert-butyl alcohol / 2 h / 0 - 30 °C
18.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere
19.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
19.2: 3 h / 0 - 30 °C / Inert atmosphere
20.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere
21.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere
22.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere
23.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere
24.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere
View Scheme
triethylsilyl chloride
994-30-9

triethylsilyl chloride

ixabepilone
219989-84-1

ixabepilone

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

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

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 40℃; for 18h;92%
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 0 - 25℃; for 2.16667h; Inert atmosphere;89%
ixabepilone
219989-84-1

ixabepilone

A

[4S-[4R*,7S*,8R*,9R*,15R*(E)]]-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-1-aza-13(Z)-cyclohexadecene-2,6-dione
219989-87-4

[4S-[4R*,7S*,8R*,9R*,15R*(E)]]-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-1-aza-13(Z)-cyclohexadecene-2,6-dione

B

[4S-[4R*,7S*,8R*,9R*,15R*(E)]]-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-1-aza-13(E)-cyclohexadecene-2,6-dione

[4S-[4R*,7S*,8R*,9R*,15R*(E)]]-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-1-aza-13(E)-cyclohexadecene-2,6-dione

Conditions
ConditionsYield
With n-butyllithium; tungsten(VI) chloride In tetrahydrofuran; hexane at 25℃; for 0.5h;A 47%
B 9.1%
phosgene
75-44-5

phosgene

2-(pyridin-2-yldisulfanyl)ethan-1-amine hydrochloride

2-(pyridin-2-yldisulfanyl)ethan-1-amine hydrochloride

ixabepilone
219989-84-1

ixabepilone

C35H50N4O6S3

C35H50N4O6S3

Conditions
ConditionsYield
Stage #1: phosgene; ixabepilone With triethylamine In dichloromethane; toluene for 0.5h;
Stage #2: 2-(pyridin-2-yldisulfanyl)ethan-1-amine hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane; toluene for 1h;
49%
octadecanedioic acid mono-triisopropylsilyl ester

octadecanedioic acid mono-triisopropylsilyl ester

ixabepilone
219989-84-1

ixabepilone

C54H94N2O8SSi

C54H94N2O8SSi

Conditions
ConditionsYield
Stage #1: ixabepilone With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 0℃; for 0.166667h;
Stage #2: octadecanedioic acid mono-triisopropylsilyl ester In dichloromethane at 0 - 20℃;
6-(2,2,2-trichloroethoxycarbonylamino)hexanoic acid
130332-90-0

6-(2,2,2-trichloroethoxycarbonylamino)hexanoic acid

ixabepilone
219989-84-1

ixabepilone

A

C36H54Cl3N3O8S

C36H54Cl3N3O8S

B

C36H54Cl3N3O8S

C36H54Cl3N3O8S

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h; Inert atmosphere;
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

ixabepilone
219989-84-1

ixabepilone

A

7-tert-butyl dimethylsilyl ixabepilone

7-tert-butyl dimethylsilyl ixabepilone

B

C33H56N2O5SSi

C33H56N2O5SSi

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;
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