|
【结 构 式】 
|
【分子编号】61498 【品名】methyl 2-{(2R,3S,4R,5R)-3,4-bis(benzoyloxy)-5-[(benzoyloxy)methyl]tetrahydro-2-furanyl}-4,5-dihydro-1,3-thiazole-4-carboxylate 【CA登记号】 |
【 分 子 式 】C31H27NO9S 【 分 子 量 】589.62272 【元素组成】C 63.15% H 4.62% N 2.38% O 24.42% S 5.44% |
合成路线1
该中间体在本合成路线中的序号：(IV)The reaction of 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (I) with Tms-CN and SnCl4 in dichloromethane gives the carbonitrile (II), which is cyclized with L-cysteine methyl ester (III) by means of TEA in dichloromethane to yield the thiazoline carboxylate (IV). The dehydrogenation of (IV) by means of BrCCl3 and DBU in the same solvent affords the thiazole carboxylate (V), which is finally treated with ammonia in methanol to hydrolyze the benzoate groups and form the carboxamide residue of the target tiazofurin.
| 【1】 Brown, R.S.; et al.; A concise route to tiazofurin. Tetrahedron Lett 2002, 43, 37, 6561. |
| 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) | 61497 | (2S,3R,4R,5R)-2-(acetyloxy)-4-(benzoyloxy)-5-[(benzoyloxy)methyl]tetrahydro-3-furanyl benzoate | C28H24O9 | 详情 | 详情 | |
| (II) | 29143 | (2S,3S,4R,5R)-4-(benzoyloxy)-5-[(benzoyloxy)methyl]-2-cyanotetrahydro-3-furanyl benzoate | C27H21NO7 | 详情 | 详情 | |
| (III) | 27413 | methyl (2R)-2-amino-3-sulfanylpropanoate | C4H9NO2S | 详情 | 详情 | |
| (IV) | 61498 | methyl 2-{(2R,3S,4R,5R)-3,4-bis(benzoyloxy)-5-[(benzoyloxy)methyl]tetrahydro-2-furanyl}-4,5-dihydro-1,3-thiazole-4-carboxylate | C31H27NO9S | 详情 | 详情 | |
| (V) | 61499 | methyl 2-{(2R,3S,4R,5R)-3,4-bis(benzoyloxy)-5-[(benzoyloxy)methyl]tetrahydro-2-furanyl}-1,3-thiazole-4-carboxylate | C31H25NO9S | 详情 | 详情 |