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 -Drug Synthesis Database

【结构式】

【分子编号】46546

【品名】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

【CA登记号】

【分子式】C₂₁H₂₅NO₇S

【分子量】435.49804

【元素组成】C 57.92% H 5.79% N 3.22% O 25.72% S 7.36%

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：(III)

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.

参考文献中间体

合成目标

【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	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

Extended Information