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【结 构 式】 
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【分子编号】32005 【品名】(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-15-[(tributylsilyl)oxy]-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate 【CA登记号】 |
【 分 子 式 】C49H78O11Si2 【 分 子 量 】899.32272 【元素组成】C 65.44% H 8.74% O 19.57% Si 6.25% |
合成路线1
该中间体在本合成路线中的序号：(XVIII)The debenzylation of (XVI) by hydrogenation, and subsequent reaction with triphosgene afforded the cyclic carbonate (XVII), which was acetylated with acetic anhydride and treated with phenyllithium in THF to open the cyclic carbonate giving the benzoate (XVIII). Compound (XVIII) was submitted to a deprotection protection cycle, first with HF and pyridine followed by a treatment with Troc-Cl in the same solvent, providing intermediate (XIX). Finally, compound (XIX) was desilylated with TASF in THF, condensed with azetidinone (XX) and deprotected with Zn/acetic acid to provide taxol.
| 【1】 Morihira, K.; et al.; Enantioselective total synthesis of Taxol. J Am Chem Soc 1998, 120, 49, 12980. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XVI) | 32003 | (1S,3S,5S,6R,7S,10R,12S,13S,15R,18S)-7-hydroxy-13,17,20,20-tetramethyl-14-oxo-3-phenyl-18-[(tributylsilyl)oxy]-12-[(triethylsilyl)oxy]-2,4,9-trioxapentacyclo[14.3.1.0(1,5).0(6,13).0(7,10)]icos-16-en-15-yl acetate | C47H76O9Si2 | 详情 | 详情 | |
| (XVII) | 32004 | (1S,5S,6R,7S,10R,12S,13S,15R,18S)-7-hydroxy-13,17,20,20-tetramethyl-3,14-dioxo-18-[(tributylsilyl)oxy]-12-[(triethylsilyl)oxy]-2,4,9-trioxapentacyclo[14.3.1.0(1,5).0(6,13).0(7,10)]icos-16-en-15-yl acetate | C41H70O10Si2 | 详情 | 详情 | |
| (XVIII) | 32005 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-15-[(tributylsilyl)oxy]-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | C49H78O11Si2 | 详情 | 详情 | |
| (XIX) | 32006 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-15-[(tributylsilyl)oxy]-9-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | C46H65Cl3O13Si | 详情 | 详情 | |
| (XX) | 10490 | (3R,4S)-1-Benzoyl-4-phenyl-3-[(triethylsilyl)oxy]-2-azetanone | C22H27NO3Si | 详情 | 详情 |