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Epothilone D

Epothilone D

CAS号：189453-10-9

英文名：epothilone D

分子式

C26H39NO5S

熔点

密度

分子量

477.657

沸点

溶解度

信号词

危险品标志

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化合物简介

Epothilones are polyketide natural products that inhibit cancer cells by a mechanism similar to paclitaxel, and also are effective against paclitaxel-resistant tumours. Epothilone D is in phase I clinical testing of in patients with advanced solid tumours. Epothilone D is a cytotoxic macrolide that stabilises malignant cells' microtubules and arrests mitosis, a characteristic it shares with other epothilones. They bind to the same hepatic sites as does paclitaxel (Taxol) in a 1:1 stoichiometric ratio of a, b-tubulin heterodimers.

基本信息

中文名称

Epothilone D

英文名称

epothilone D

中文别名

埃博霉素、埃博霉素 D

英文别名

Epothilones、Epothilon A、desoxyepothilone B、Epo A、epithilone A、Epothilone D

CAS号

189453-10-9

分子式

C26H39NO5S

分子量

477.657

精确质量

477.255

PSA

124.96

LOGP

4.8762

编号系统

UNII

T0358E0YUF

合成路线

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(4S,7R,8S,9S,13Z,16S)-4,8-二-{[叔-丁基(二甲基)硅烷基]氧基}-5,5,7,9,13-五甲基-16-[(E)-1-甲基-2-(2-甲基-1,3-噻唑-4-基)乙烯基]氧代环己癸-13-烯-2,6-二酮

(4S,7R,8S,9S,13Z,16S)-4,8-二-{[叔-丁基(二甲基)硅烷基]氧基}-5,5,7,9,13-五甲基-16-[(E)-1-甲基-2-(2-甲基-1,3-噻唑-4-基)乙烯基]氧代环己癸-13-烯-2,6-二酮

Epothilone D

上游原料

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(2E)-2-Methyl-3-(2-methyl-1,3-thiazol-4-yl)acrylaldehyde

(2E)-2-Methyl-3-(2-methyl-1,3-thiazol-4-yl)acrylaldehyde

(2S,6Z,9S,10E)-9-{[tert-butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)undeca-6,10-dienal

(2S,6Z,9S,10E)-9-{[tert-butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)undeca-6,10-dienal

(2S,3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-[1,3]dithian-2-yl-2,4,6-trimethyl-5-triphenylsilanyloxy-heptan-1-ol

(2S,3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-[1,3]dithian-2-yl-2,4,6-trimethyl-5-triphenylsilanyloxy-heptan-1-ol

2,2-Dimethyl-3-oxopentanal

2,2-Dimethyl-3-oxopentanal

(4S,7R,8S,9S,13Z,16S)-4,8-二-{[叔-丁基(二甲基)硅烷基]氧基}-5,5,7,9,13-五甲基-16-[(E)-1-甲基-2-(2-甲基-1,3-噻唑-4-基)乙烯基]氧代环己癸-13-烯-2,6-二酮

(4S,7R,8S,9S,13Z,16S)-4,8-二-{[叔-丁基(二甲基)硅烷基]氧基}-5,5,7,9,13-五甲基-16-[(E)-1-甲基-2-(2-甲基-1,3-噻唑-4-基)乙烯基]氧代环己癸-13-烯-2,6-二酮

(3S,6R,7S,8S,12Z,15S,16E)-3,7,15-三-{[叔-丁基(二甲基)硅烷基]氧基}-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)-5-氧代-十七-12,16-二烯酸

(3S,6R,7S,8S,12Z,15S,16E)-3,7,15-三-{[叔-丁基(二甲基)硅烷基]氧基}-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)-5-氧代-十七-12,16-二烯酸

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埃博霉素B

上游原料

(2E)-2-Methyl-3-(2-methyl-1,3-thiazol-4-yl)acrylaldehyde (2S,6Z,9S,10E)-9-{[tert-butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-11-(2-methyl-1,3-thiazol-4-yl)undeca-6,10-dienal (2S,3S,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-[1,3]dithian-2-yl-2,4,6-trimethyl-5-triphenylsilanyloxy-heptan-1-ol 2,2-Dimethyl-3-oxopentanal (4S,7R,8S,9S,13Z,16S)-4,8-二-{[叔-丁基(二甲基)硅烷基]氧基}-5,5,7,9,13-五甲基-16-[(E)-1-甲基-2-(2-甲基-1,3-噻唑-4-基)乙烯基]氧代环己癸-13-烯-2,6-二酮 (3S,6R,7S,8S,12Z,15S,16E)-3,7,15-三-{[叔-丁基(二甲基)硅烷基]氧基}-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)-5-氧代-十七-12,16-二烯酸 (3R,4R,5S)-3-(2-(1,3-dithian-2-yl)propan-2-yl)-5-((S)-1-(benzyloxy)propan-2-yl)-4,7,7,8,8-pentamethyl-1,1,1-triphenyl-2,6-dioxa-1,7-disilanonane (3R,4R,5S,6S)-6-((S)-1-(benzyloxy)propan-2-yl)-3-(iodomethyl)-2-methoxy-3,5-dimethyltetrahydro-2H-pyran-4-ol (3S)-4-[7-bromo-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-hepta-1,5-dienyl]-2-methyl-thiazole (1S)-[(1E)-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethynyl]-3-butenyl acetate 2-甲基-1,3-噻唑-4-甲醛 (3S,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(4-methoxy-benzyloxy)-4,4,6,8-tetramethyl-5-oxo-nonanoic acid (1E,5Z)-(S)-2,6-Dimethyl-1-(2-methyl-thiazol-4-yl)-octa-1,5,7-trien-3-ol (3S,6R,7S,8S,12Z,15S,16E)-5-oxo-15-hydroxy-3-triethylsilanoxy-17-(2-methylthiazol-4-yl)-4,4,6,8,12,16-hexamethyl-7-(2,2,2-trichloroethoxycarbonyloxy)heptadeca-12,16-dienoic acid (1R,3S,4S,5R,6R)-3-((S)-2-Benzyloxy-1-methyl-ethyl)-4,6-dimethyl-2-oxa-bicyclo[4.1.0]heptan-5-ol (1E,3Z)-1-甲氧基-2-甲基-3-(三甲基硅氧基)-1,3-戊二烯 tert-butyl 4,4-dimethyl-3,5-dioxoheptanoate (5S)-2-iodo-6-methyl-7-(2-methylthiazol-4-yl)-5-(triethylsilyloxy)-2,6-heptadiene (4R,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2-methoxy-3,3,5-trimethyl-tetrahydro-pyran-4-ol tert-butyl (6R,7S,8S,12Z,15S,16E)-3,5-dioxo-15-hydroxy-17-(2-methylthiazol-4-yl)-4,4,6,8,12,16-hexamethyl-(2,2,2-trichloroethoxycarbonyl)pentadeca-12,16-dieno-ate (13Z,4S,7R,8S,9S,16S)-4-(tert-butyldimethylsilyloxy)-8-hydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methylthiazol-4-yl)vinyl]oxacyclohexadec-13-ene-2,6-dione (2S,3S,4R,5R)-1-(benzyloxy)-6-(1,3-dithian-2-yl)-2,4,6-trimethyl-5-((triphenylsilyl)oxy)heptan-3-ol (5S)-5-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyloct-7en-3-one S-ethyl (2S,Z)-2-((tert-butyldimethylsilyl)oxy)-5-methyl-6-((tetrahydro-2H-pyran-2-yl)oxy)hex-4-enethioate (3S,6R,7S,12Z,15S,16E)-3,7-二-{[叔-丁基(二甲基)硅烷基]氧基}-15-羟基-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)-5-氧代十七碳-12,16-二烯酸 (4S)-4-benzyl-3-((Z)-5-methyl-6-((tetrahydro-2H-pyran-2-yl)oxy)hex-4-enoyl)oxazolidin-2-one 10,11-didehydroepothilone D (S)-4-Benzyl-3-[(Z)-(S)-2-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-(tetrahydro-pyran-2-yloxy)-hex-4-enoyl]-oxazolidin-2-one (3S,6R,7S,8S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-4,4,6,8-tetramethyl-5-oxo-nonanoic acid methyl ester methyl (3S,6R,7S,8R)-3,7-bis((tert-butyldimethylsilyl)oxy)-4,4,6,8-tetramethyl-5,9-dioxononanoate (3S)-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)hexa-1,5-dien-3-ol (-)-(2Z,5S,6E)-5-{[叔-丁基(二甲基)硅烷基]氧基}-2,6-二甲基-7-(2-甲基-1,3-噻唑-4-基)庚-2,6-二烯-1-醇 (Z)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-7-(tetrahydro-pyran-2-yloxy)-hept-5-en-2-one (3S,6R,7S,8S)-3,7-bis((tert-butyldimethylsilyl)oxy)-9-((4-methoxybenzyl)oxy)-4,4,6,8-tetramethyl-5-oxononanal 12,13-deoxy-7-(2,2,2-trichloroethoxycarbonyl)-3-(triethylsilyloxy)epothilone B (2R,3R,4R,5R)-3-((tert-butyldimethylsilyl)oxy)-6-(1,3-dithian-2-yl)-2,4,6-trimethyl-5-((triphenylsilyl)oxy)heptanal (E)-9,10-dehydro-12,13-desoxyepothilone B (2S,3S,4R,7S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-2,4,6,6-tetramethyl-dec-9-en-5-one (4S,7R,8S,9S,16S)-4,8-bis((tert-butyldimethylsilyl)oxy)-5,5,7,9,13-pentamethyl-16-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)oxacyclohexadec-13-ene-2,6-dione (2S,3S,4R)-2-((S)-1-(benzyloxy)propan-2-yl)-3,5-dimethyl-3,4-dihydro-2H-pyran-4-ol (2S,3S,4R,7S)-7-((tert-butyldimethylsilyl)oxy)-3-hydroxy-1-((4-methoxybenzyl)oxy)-2,4,6,6-tetramethyldec-9-en-5-one tert-butyl (3S,6R,7S,8S,12Z,15S,16E)-5-oxo-3,15-dihydroxy-17-(2-methylthiazol-4-yl)-4,4,6,8,12,16-hexamethyl-(2,2,2-trichloroethoxycarbonyl)pentadeca-12,16-dienoate 4-((1E,3S,5Z)-3-((tert-butyldimethylsilyl)oxy)-2,6-dimethyl-7-((tetrahydro-2H-pyran-2-yl)oxy)hepta-1,5-dien-1-yl)-2-methylthiazole (4S,7R,8S,9S,16S,Z)-4-hydroxy-5,5,7,9,13-pentamethyl-16-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-2,6-dioxooxacyclohexadec-13-en-8-yl (2,2,2-trichloroethyl) carbonate [(4R,5R,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2-methoxy-3,3,5-trimethyl-tetrahydro-pyran-4-yloxy]-triphenyl-silane tert-Butyldimethylsilyl {(1S,3Z)-4-iodo-1-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-ethenyl]-3-pentenyl} ether tert-butyl (6R,7S,8S,12Z,15S,16E)-15-((tert-butyldimethylsilyl)oxy)-4,4,6,8,12,16-hexamethyl-17-(2-methylthiazol-4-yl)-3,5-dioxo-7-(((2,2,2-trichloroethoxy)carbonyl)oxy)heptadeca-12,16-dienoate

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