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【结 构 式】

【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%

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:(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
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