methyl 2-{(2R,3S,4R,5R)-3,4-bis(benzoyloxy)-5-[(benzoyloxy)methyl]tetrahydro-2-furanyl}-1,3-thiazole-4-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】61499

【品名】methyl 2-{(2R,3S,4R,5R)-3,4-bis(benzoyloxy)-5-[(benzoyloxy)methyl]tetrahydro-2-furanyl}-1,3-thiazole-4-carboxylate

【CA登记号】

【分子式】C₃₁H₂₅NO₉S

【分子量】587.60684

【元素组成】C 63.37% H 4.29% N 2.38% O 24.51% S 5.46%

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：(V)

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.

参考文献中间体

合成目标

【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	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

Extended Information