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【结 构 式】 
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【分子编号】54926 【品名】(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-2-(benzoyloxy)-1,15-dihydroxy-9-[(1H-imidazol-1-ylcarbonyl)oxy]-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-12-yl 1H-imidazole-1-carboxylate 【CA登记号】 |
【 分 子 式 】C37H40N4O12 【 分 子 量 】732.74436 【元素组成】C 60.65% H 5.5% N 7.65% O 26.2% |
合成路线1
该中间体在本合成路线中的序号：(II)The acylation of 10-deacetylbaccatin III (I) with CDI in chloroform gives the 7,10-bis-O-(imidazolylcarbonyl) derivative (II), which is condensed with the chiral oxazolidinecarboxylic acid (III) by means of DCC and DMAP in hot toluene to yield the corresponding ester (IV). The hydrolysis of (IV) with aqueous TFA affords compound (V), which is finally treated with (Boc)2O and NaHCO3 in THF to provide the target docetaxel.
| 【1】 Duvvuri, S.; Puranik, R. (Dr. Reddy's Research Foundation); An improved process for the preparation of docetaxel. WO 0212216 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 10467 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,9,12,15-tetrahydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | 32981-86-5 | C29H36O10 | 详情 | 详情 |
| (II) | 54926 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-2-(benzoyloxy)-1,15-dihydroxy-9-[(1H-imidazol-1-ylcarbonyl)oxy]-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-12-yl 1H-imidazole-1-carboxylate | C37H40N4O12 | 详情 | 详情 | |
| (III) | 10551 | (4S,5R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-phenyl-1,3-oxazolane-5-carboxylic acid | C17H23NO5 | 详情 | 详情 | |
| (IV) | 54927 | 5-{(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-2-(benzoyloxy)-1-hydroxy-9,12-bis[(1H-imidazol-1-ylcarbonyl)oxy]-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-15-yl} 3-(tert-butyl) (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate | C54H61N5O16 | 详情 | 详情 | |
| (V) | 12497 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-15-[[(2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl]oxy]-1,9,12-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | C38H45NO12 | 详情 | 详情 |