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【结 构 式】 
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【分子编号】46544 【品名】[(3aR,4R,6S,6aS)-6-cyano-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl benzoate 【CA登记号】 |
【 分 子 式 】C16H17NO5 【 分 子 量 】303.31472 【元素组成】C 63.36% H 5.65% N 4.62% O 26.37% |
合成路线1
该中间体在本合成路线中的序号：(I)A new synthesis of tiazofurin has been reported: The cyclization of 5-O-benzoyl-2,3-O-isopropylidene-beta-D-ribofuranosyl-1-carbonitrile (I) with cysteine ethyl ester (II) by means of TEA in dichloromethane gives the thiazoline derivative (III), which is dehydrogenated with MnO2 in the same solvent to yield the corresponding thiazole derivative (IV). Removal of the isopropylidene protecting group of (IV) with TFA in THF/water affords 2-(5'-O-benzoyl-beta-D-ribofuranosyl)thiazole-4-carboxylic acid ethyl ester (V), which is finally debenzoylated and amidated by reaction with ammonia in methanol.
| 【1】 Ramasamy, K.S.; Bandaru, R.; Alverett, D.; A new synthetic methodology for tiazofurin. J Org Chem 2000, 65, 18, 5849. |
| 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) | 46544 | [(3aR,4R,6S,6aS)-6-cyano-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl benzoate | C16H17NO5 | 详情 | 详情 | |
| (II) | 46545 | ethyl 2-amino-3-sulfanylpropanoate | C5H11NO2S | 详情 | 详情 | |
| (III) | 46546 | ethyl 2-[(3aS,4R,6R,6aR)-6-[(benzoyloxy)methyl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-4,5-dihydro-1,3-thiazole-4-carboxylate | C21H25NO7S | 详情 | 详情 | |
| (IV) | 46547 | ethyl 2-[(3aS,4R,6R,6aR)-6-[(benzoyloxy)methyl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1,3-thiazole-4-carboxylate | C21H23NO7S | 详情 | 详情 | |
| (V) | 46548 | ethyl 2-[(2R,3R,4S,5R)-5-[(benzoyloxy)methyl]-3,4-dihydroxytetrahydro-2-furanyl]-1,3-thiazole-4-carboxylate | C18H19NO7S | 详情 | 详情 |