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【结 构 式】

【分子编号】29622

【品名】(2R,3R,4S,5R)-2,4-bis(acetoxy)-5-[(acetoxy)methyl]tetrahydro-3-thiophenyl acetate

【CA登记号】

【 分 子 式 】C13H18O8S

【 分 子 量 】334.34712

【元素组成】C 46.7% H 5.43% O 38.28% S 9.59%

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:(IX)

An alternative procedure consisted in the condensation of tetraacetyl 4-thio-D-ribofuranose (IX) with silylated cytosine (IV) in the presence of SnCl4. After chromatographic separation of the major beta-nucleoside (X), deprotection of its acetyl groups with methanolic ammonia yielded the ribofuranoside (XI). In order to achieve the required epimerization of the 2'-hydroxyl group of (XI), cyclization between the 2 and 2' positions by means of POCl3 in DMF produced the cyclic derivative (XII). Finally, ring opening of (XII) by aqueous ammonia yielded the target arabinofuranosyl derivative.

1 Whistler, R.L.; Ototani, N.; Preparation and antitumor activity of 4'-thio analogs of 2,2'-anhydro-1-beta-D-arabinofuranosylcytosine. J Med Chem 1974, 17, 5, 535.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 29617 N-(trimethylsilyl)-N-[2-[(trimethylsilyl)oxy]-4-pyrimidinyl]acetamide C12H23N3O2Si2 详情 详情
(IX) 29622 (2R,3R,4S,5R)-2,4-bis(acetoxy)-5-[(acetoxy)methyl]tetrahydro-3-thiophenyl acetate C13H18O8S 详情 详情
(X) 29623 (2R,3R,4S,5R)-2-[4-(acetamido)-2-oxo-1(2H)-pyrimidinyl]-4-(acetoxy)-5-[(acetoxy)methyl]tetrahydro-3-thiophenyl acetate C17H21N3O8S 详情 详情
(XI) 29624 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-thiophenyl]-2(1H)-pyrimidinone C9H13N3O4S 详情 详情
(XII) 29625 (2R,3S,9aR)-2-(hydroxymethyl)-6-imino-2,3,3a,9a-tetrahydro-6H-thieno[2',3':4,5][1,3]oxazolo[3,2-a]pyrimidin-3-ol C9H11N3O3S 详情 详情
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