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【结 构 式】 
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【分子编号】64993 【品名】methyl 3,4,5-tris(acetyloxy)-6-{[2-(methylamino)-4-nitrophenyl]oxy}tetrahydro-2H-pyran-2-carboxylate 【CA登记号】 |
【 分 子 式 】C20H24N2O12 【 分 子 量 】484.41684 【元素组成】C 49.59% H 4.99% N 5.78% O 39.63% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(I)The protected glucuronic acid derivative (I) is hydrolyzed under alkaline conditions to furnish (II). The alcoholic hydroxyl groups of (II) are subsequently protected as the silyl ether (III) employing t-butyldimethylsilyl triflate in the presence of DMAP. The carboxyl group of (III) is further converted to the corresponding benzyl ester (IV) by DCC-mediated coupling with benzyl alcohol. Acylation of amine (IV) with phosgene leads to the carbamyl chloride (V). (1,2)
| 【1】 Schmidt, F.; Monneret, C.; Prodrug mono therapy: Synthesis and biological evaluation of an etoposide glucuronide-prodrug. Bioorg Med Chem 2003, 11, 10, 2277. |
| 【2】 Monneret, C.; Schmidt, F. (CNRS (Centre National de la Recherche Scientifique); Institut Curie); Derivs. of etoposide and analogs, and pharmaceutical compsns. containing them. WO 0335661 . |
| 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) | 64993 | methyl 3,4,5-tris(acetyloxy)-6-{[2-(methylamino)-4-nitrophenyl]oxy}tetrahydro-2H-pyran-2-carboxylate | C20H24N2O12 | 详情 | 详情 | |
| (II) | 64994 | 3,4,5-trihydroxy-6-{[2-(methylamino)-4-nitrophenyl]oxy}tetrahydro-2H-pyran-2-carboxylic acid | C13H16N2O9 | 详情 | 详情 | |
| (III) | 64995 | 3,4,5-tris{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-6-{[2-(methylamino)-4-nitrophenyl]oxy}tetrahydro-2H-pyran-2-carboxylic acid | C31H58N2O9Si3 | 详情 | 详情 | |
| (IV) | 64996 | phenylmethyl 3,4,5-tris{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-6-{[2-(methylamino)-4-nitrophenyl]oxy}tetrahydro-2H-pyran-2-carboxylate | C38H64N2O9Si3 | 详情 | 详情 | |
| (V) | 64997 | phenylmethyl 6-({2-[(chlorocarbonyl)(methyl)amino]-4-nitrophenyl}oxy)-3,4,5-tris{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}tetrahydro-2H-pyran-2-carboxylate | C39H63ClN2O10Si3 | 详情 | 详情 |
Extended Information