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【结 构 式】 
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【分子编号】49340 【品名】5-[(1S,2S,3R,4S,7R,9S,11R,13R,16S)-4,13-bis(acetoxy)-2-(benzoyloxy)-1-hydroxy-15,18,18-trimethyl-12-oxo-6-oxapentacyclo[12.3.1.0(3,11).0(4,7).0(9,11)]octadec-14-en-16-yl] 3-(tert-butyl) (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate 【CA登记号】 |
【 分 子 式 】C48H57NO14 【 分 子 量 】871.97892 【元素组成】C 66.12% H 6.59% N 1.61% O 25.69% |
合成路线1
该中间体在本合成路线中的序号：(III)The reaction of the taxane derivative (I) with trifluoromethanesulfonic anhydride gives the monotriflate (II), which is treated with sodium azide in hot acetonitrile to yield the cyclopropa derivative (III). The cleavage of the oxazolidine ring of (III) by means of formic acid affords the 3-amino-2-hydroxy derivative (IV), which is finally acylated with tert-butoxycarbonyl anhydride to provide the target taxoid derivative.
| 【1】 Bouchard, H.; Buourzat, J.-D.; Commercon, A. (Aventis Pharma SA); Novel taxoids, preparation thereof and pharmaceutical compsns. containing same. EP 0673372; FR 2698871; JP 1996504425; JP 1998291930; US 5814658; WO 9413654 . |
| 【2】 Renard, A.; Bissery, M.-C. (Aventis Pharma SA); Method for treating abnormal cell proliferation in the brain. US 6156789 . |
| 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) | 49338 | 5-[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-2-(benzoyloxy)-1,9-dihydroxy-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 | C48H59NO15 | 详情 | 详情 | |
| (II) | 49339 | 5-((1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-2-(benzoyloxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-[[(trifluoromethyl)sulfonyl]oxy]-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 | C49H58F3NO17S | 详情 | 详情 | |
| (III) | 49340 | 5-[(1S,2S,3R,4S,7R,9S,11R,13R,16S)-4,13-bis(acetoxy)-2-(benzoyloxy)-1-hydroxy-15,18,18-trimethyl-12-oxo-6-oxapentacyclo[12.3.1.0(3,11).0(4,7).0(9,11)]octadec-14-en-16-yl] 3-(tert-butyl) (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate | C48H57NO14 | 详情 | 详情 | |
| (IV) | 39341 | methyl 2-(5-chloro-2-methoxyphenyl)acetate | C10H11ClO3 | 详情 | 详情 |