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【结 构 式】 
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【分子编号】29618 【品名】[(2R,3S,4S,5R)-5-[4-(acetamido)-2-oxo-1(2H)-pyrimidinyl]-3,4-bis(benzoyloxy)tetrahydro-2-thiophenyl]methyl benzoate 【CA登记号】 |
【 分 子 式 】C32H27N3O8S 【 分 子 量 】613.6478 【元素组成】C 62.63% H 4.43% N 6.85% O 20.86% S 5.23% |
合成路线1
该中间体在本合成路线中的序号：(V)Methyl 4-thio-beta-D-arabinofuranoside (I) was converted to the tribenzoate ester (II) by means of benzoyl chloride and pyridine, and then treated with HBr in AcOH to give the arabinofuranosyl bromide (III). Displacement of bromide ion in (III) by bis(trimethylsilyl)-N-acetylcytosine (IV) at 130 C led to an anomeric mixture of nucleosides from which the required beta-anomer (V) was isolated by chromatography. Finally, deprotection of the benzoate esters and acetamido group of (V) was performed with methanolic ammonia at 0 C.
| 【1】 Whistler, R.L.; et al.; 4-Thio-D-arabinofuranosylpyrimidine nucleosides. J Org Chem 1971, 36, 1, 108. |
| 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) | 29614 | (2R,3S,4S,5R)-2-(hydroxymethyl)-5-methoxytetrahydro-3,4-thiophenediol | C6H12O4S | 详情 | 详情 | |
| (II) | 29615 | [(2R,3S,4S,5R)-3,4-bis(benzoyloxy)-5-methoxytetrahydro-2-thiophenyl]methyl benzoate | C27H24O7S | 详情 | 详情 | |
| (III) | 29616 | [(2R,3S,4S,5S)-3,4-bis(benzoyloxy)-5-bromotetrahydro-2-thiophenyl]methyl benzoate | C26H21BrO6S | 详情 | 详情 | |
| (IV) | 29617 | N-(trimethylsilyl)-N-[2-[(trimethylsilyl)oxy]-4-pyrimidinyl]acetamide | C12H23N3O2Si2 | 详情 | 详情 | |
| (V) | 29618 | [(2R,3S,4S,5R)-5-[4-(acetamido)-2-oxo-1(2H)-pyrimidinyl]-3,4-bis(benzoyloxy)tetrahydro-2-thiophenyl]methyl benzoate | C32H27N3O8S | 详情 | 详情 |