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【结 构 式】 
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【分子编号】32012 【品名】(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-2-(benzoyloxy)-9-[(tert-butoxycarbonyl)oxy]-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-15-yl (4S,5R)-2,4-diphenyl-4,5-dihydro-1,3-oxazole-5-carbox 【CA登记号】 |
【 分 子 式 】C52H57NO15 【 分 子 量 】936.02232 【元素组成】C 66.73% H 6.14% N 1.5% O 25.64% |
合成路线1
该中间体在本合成路线中的序号：(VIII)3) The selective protection of baccatin III (I) with tert-butoxycarbonyl anhydride and Li-HMDS in DMF gives 7-O-(tert-butoxycarbonyl)baccatin III (VII), which is condensed with the chiral oxazolidine (III) by means of DCC and DMAP in toluene affording the 13-O-oxazolidinyl derivative (VIII). Finally, this compound is deprotected with formic or acetic acids, and the oxazolidine ring is cleaved with trifluoroacetic acid/acetic acid.
| 【1】 Gibson, F.S. (Bristol-Myers Squibb Co.); Synthesis of paclitaxel baccatin III by protecting the 7-hydroxyl using a strong base and an electrophile. WO 9945001 . |
| 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) | 10447 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-1,9,15-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 | C31H38O11 | 详情 | 详情 | |
| (III) | 10597 | (4S,5R)-2,4-Diphenyl-4,5-dihydro-1,3-oxazole-5-carboxylic acid | C16H13NO3 | 详情 | 详情 | |
| (VII) | 32011 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-9-[(tert-butoxycarbonyl)oxy]-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | C36H46O13 | 详情 | 详情 | |
| (VIII) | 32012 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-2-(benzoyloxy)-9-[(tert-butoxycarbonyl)oxy]-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-15-yl (4S,5R)-2,4-diphenyl-4,5-dihydro-1,3-oxazole-5-carbox | C52H57NO15 | 详情 | 详情 |