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【结 构 式】 
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【分子编号】26489 【品名】5-[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-2-(benzoyloxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-12-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-15-yl] 3-(tert-butyl) (4S,5R)-4-cyclopropyl-2-(4-methoxyphenyl)-1,3-oxazolidine-3,5-dicarboxylate 【CA登记号】 |
【 分 子 式 】C57H74Cl3NO17Si 【 分 子 量 】1179.6547 【元素组成】C 58.04% H 6.32% Cl 9.02% N 1.19% O 23.06% Si 2.38% |
合成路线1
该中间体在本合成路线中的序号：(XXXI)In a further procedure, hydroxy amino ester (VIII) was treated with anisaldehyde dimethyl acetal (XXVII) to provide oxazolidine (XXVIII) as a diastereomeric mixture. Ester hydrolysis of (XXVIII) with LiOH gave acid (XXIX), which was then coupled with taxane (XXX) to furnish ester (XXXI). Acidic treatment of (XXXI) cleaved the oxazolidine and deprotected the silyl ether group to produce (XXXII). Subsequent coupling of (XXXII) with acid (XXVII), followed by reductive deprotection of the trichloroethylcarbonyl group, provided intermediate (XXVI), which was finally converted into the title compound by hydrogenolysis in the presence of p-TsOH as above.
| 【1】 Tsujihari, K.; Hashiyama, T.; Ohashi, M.; Nakanishi, N. (Tanabe Seiyaku Co., Ltd.); Baccatin derivs. and processes for preparing the same. CA 2162759; EP 0712854; JP 1997151181; US 5589502 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VIII) | 26469 | methyl (2R,3S)-3-[(tert-butoxycarbonyl)amino]-3-cyclopropyl-2-hydroxypropanoate | C12H21NO5 | 详情 | 详情 | |
| (XXVI) | 26484 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-2-(benzoyloxy)-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-15-yl (5S,12R)-5-(aminocarbonyl)-12-[(S)-[(tert-butoxycarbonyl)amino](cyclopropyl)methyl]-3,7,10-trioxo-1-phenyl-2,8,11-trioxa-4-azatridecan-13-oate | C54H67N3O20 | 详情 | 详情 | |
| (XXVII) | 26485 | 1-(dimethoxymethyl)-4-methoxybenzene | 2186-92-7 | C10H14O3 | 详情 | 详情 |
| (XXVIII) | 26486 | 3-(tert-butyl) 5-methyl (4S,5R)-4-cyclopropyl-2-(4-methoxyphenyl)-1,3-oxazolidine-3,5-dicarboxylate | C20H27NO6 | 详情 | 详情 | |
| (XXIX) | 26487 | (4S,5R)-3-(tert-butoxycarbonyl)-4-cyclopropyl-2-(4-methoxyphenyl)-1,3-oxazolidine-5-carboxylic acid | C19H25NO6 | 详情 | 详情 | |
| (XXX) | 26488 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-12-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | C38H51Cl3O12Si | 详情 | 详情 | |
| (XXXI) | 26489 | 5-[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-2-(benzoyloxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-12-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-15-yl] 3-(tert-butyl) (4S,5R)-4-cyclopropyl-2-(4-methoxyphenyl)-1,3-oxazolidine-3,5-dicarboxylate | C57H74Cl3NO17Si | 详情 | 详情 | |
| (XXXII) | 26490 | (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-15-([(2R,3S)-3-[(tert-butoxycarbonyl)amino]-3-cyclopropyl-2-hydroxypropanoyl]oxy)-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-12-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate | C43H54Cl3NO16 | 详情 | 详情 | |
| (XXXIII) | 26491 | 2-[((3S)-4-amino-3-[[(benzyloxy)carbonyl]amino]-4-oxobutanoyl)oxy]acetic acid | C14H16N2O7 | 详情 | 详情 |