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【结 构 式】 
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【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% |
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 |