【结 构 式】 |
【分子编号】25334 【品名】(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-([(2R,3S)-3-[(tert-butoxycarbonyl)amino]-3-phenyl-2-[(triisopropylsilyl)oxy]propanoyl]oxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]h 【CA登记号】 |
【 分 子 式 】C60H89NO15Si2 【 分 子 量 】1120.5354 【元素组成】C 64.31% H 8.01% N 1.25% O 21.42% Si 5.01% |
合成路线1
该中间体在本合成路线中的序号:(IV)Selective protection of the 7-hydroxyl group of deacetylbaccatin (I) with triethylsilyl chloride provided silyl ether (II), which was acetylated at position 10 using acetyl chloride and lithium hexamethyldisilazide. Further coupling of (II) with beta-lactam (III) gave (IV), which by selective removal of the 7-silyl group with 0.1 N HCl gave 10-acetyl-2'-(triisopropylsilyl)docetaxel (V). This was condensed with benzoylcinnamic acid (VI) employing EDC and DMAP to afford ester (VII).
【1】 Ahern, D.G.; Ojima, I.; Bounaud, P.-Y.; New photoaffinity analogs of paclitaxel. Bioorg Med Chem Lett 1999, 9, 8, 1189. |
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) | 25331 | 3-hydroxyacetophenone; 1-(3-hydroxyphenyl)-1-ethanone | 121-71-1 | C8H8O2 | 详情 | 详情 |
(II) | 25332 | (E)-3-(3,4-dimethoxyphenyl)-1-(3-hydroxyphenyl)-2-propen-1-one | C17H16O4 | 详情 | 详情 | |
(III) | 25333 | tert-butyl (3R,4S)-2-oxo-4-phenyl-3-[(triisopropylsilyl)oxy]-1-azetidinecarboxylate | C23H37NO4Si | 详情 | 详情 | |
(IV) | 25334 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-([(2R,3S)-3-[(tert-butoxycarbonyl)amino]-3-phenyl-2-[(triisopropylsilyl)oxy]propanoyl]oxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]h | C60H89NO15Si2 | 详情 | 详情 | |
(V) | 25335 | (1S,2S,3R,4S,7R,9S,10R,12R,15S)-4,12-bis(acetoxy)-15-([(2R,3S)-3-[(tert-butoxycarbonyl)amino]-3-phenyl-2-[(triisopropylsilyl)oxy]propanoyl]oxy)-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl | C54H75NO15Si | 详情 | 详情 | |
(VI) | 25336 | (E)-3-(3-benzoylphenyl)-2-propenoic acid | C16H12O3 | 详情 | 详情 | |
(VII) | 25337 | (1S,2S,3R,4S,7R,9S,10R,12R,15S)-4,12-bis(acetoxy)-9-[[(E)-3-(3-benzoylphenyl)-2-propenoyl]oxy]-15-([(2R,3S)-3-[(tert-butoxycarbonyl)amino]-3-phenyl-2-[(triisopropylsilyl)oxy]propanoyl]oxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[1 | C70H85NO17Si | 详情 | 详情 |