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
Cas:219989-84-1
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inquiryWelcome 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
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inquiryIxabepilone 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-
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inquiry1. 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
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inquiryOur main production base is located in Xuzhou industry park. We are certified both to the ISO 9001 and ISO 14001 Standards, have a safety management system in place.Our R&D team masters core technology for process-design of target building block
Our advantages: 1. All inquiries will be replied within 12 hours. 2. Dedication to quality, supply & service. 3. Strictly on selecting raw materials. 4. Reasonable & competitive price, fast lead time. 5. Sample is available for your eva
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inquiryWITH US,YOUR MONEY IN SAFE,YOUR BUSINESS IN SAFE 1)Quick Response Within 12 hours; 2)Quality Guarantee: All products are strictly tested by our QC, confirmed by QA and approved by third party lab in China, USA, Canada, Germany, UK, Italy, France et
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inquiry1. 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
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inquiry1. 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;
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
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inquiry1.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
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inquiryIXABEPILONE 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
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inquiryHello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai
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inquiry1,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
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inquiry1)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;
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inquiryHenan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod
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inquiryAppearance: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
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inquiryOur 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
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inquirySpecification:USP/EP Month production ablity:50kg/Month Low price& High quality Manufacturer Appearance:white powder Storage:Room Temperature Application:219989-84-1
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-
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inquiryHangzhou 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
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inquiryJ&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
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
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
Cas:219989-84-1
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inquiryHigh 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
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inquiryEstablished 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
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
Cas:219989-84-1
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inquiryProduct Details Grade: pharmaceutical grade Purity:99%+ ProductionCapacity: 1000 Kilogram/Month Scope of use: For scientific research only(The product must be used legally) Our Advantage 1. Best quality with competitive price. 2. Quick shipping,
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
Cas:219989-84-1
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inquiryOur 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
[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
Conditions | Yield |
---|---|
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 |
ixabepilone
Conditions | Yield |
---|---|
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
ixabepilone
Conditions | Yield |
---|---|
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
ixabepilone
Conditions | Yield |
---|---|
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
ixabepilone
Conditions | Yield |
---|---|
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
ixabepilone
Conditions | Yield |
---|---|
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
ixabepilone
Conditions | Yield |
---|---|
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
ixabepilone
Conditions | Yield |
---|---|
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
ixabepilone
Conditions | Yield |
---|---|
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 |
ixabepilone
Conditions | Yield |
---|---|
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
ixabepilone
Conditions | Yield |
---|---|
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
ixabepilone
Conditions | Yield |
---|---|
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
ixabepilone
Conditions | Yield |
---|---|
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
ixabepilone
Conditions | Yield |
---|---|
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
ixabepilone
Conditions | Yield |
---|---|
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
ixabepilone
Conditions | Yield |
---|---|
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
ixabepilone
Conditions | Yield |
---|---|
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 |
ixabepilone
Conditions | Yield |
---|---|
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 |
ixabepilone
Conditions | Yield |
---|---|
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
ixabepilone
Conditions | Yield |
---|---|
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 |
ixabepilone
Conditions | Yield |
---|---|
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
ixabepilone
Conditions | Yield |
---|---|
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 |
ixabepilone
Conditions | Yield |
---|---|
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 |
ixabepilone
Conditions | Yield |
---|---|
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 |
ixabepilone
Conditions | Yield |
---|---|
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
ixabepilone
Conditions | Yield |
---|---|
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
ixabepilone
Conditions | Yield |
---|---|
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 |
ixabepilone
Conditions | Yield |
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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
ixabepilone
Conditions | Yield |
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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 |
ixabepilone
Conditions | Yield |
---|---|
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
ixabepilone
Conditions | Yield |
---|---|
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
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
Conditions | Yield |
---|---|
With n-butyllithium; tungsten(VI) chloride In tetrahydrofuran; hexane at 25℃; for 0.5h; | A 47% B 9.1% |
phosgene
ixabepilone
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
ixabepilone
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h; Inert atmosphere; |
tert-butyldimethylsilyl chloride
ixabepilone
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere; |
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