methyl 1-{(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-[(acetyloxy)methyl]tetrahydro-2-furanyl}-1H-1,2,4-triazole-3-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】60539

【品名】methyl 1-{(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-[(acetyloxy)methyl]tetrahydro-2-furanyl}-1H-1,2,4-triazole-3-carboxylate

【CA登记号】

【分子式】C₁₅H₁₉N₃O₉

【分子量】385.33068

【元素组成】C 46.76% H 4.97% N 10.9% O 37.37%

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)

The condensation of tetraacetyl-D-ribose (I) with 1H-1,2,4-triazole-3-carboxylic acid methyl ester (II) by means of SnCl4 in refluxing dichloromethane gives -(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxylic acid methyl ester (III), which is hydrolyzed by means of NaOMe in methanol to yield the deacetylated ester (IV). Finally, this compound is treated with gaseous ammonia in methanol to afford the target amide.

参考文献中间体

合成目标

【1】 Frigerio, M.; Banfi, A.; Dall'Oro, B.; Mancini, A. (Clariant Life Science Molecules SpA); Process for the preparation of ribavirin. EP 1281715; WO 0311883; WO 0311884 .

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)	60541	(2R,3R,4R)-4,5-bis(acetyloxy)-2-[(acetyloxy)methyl]tetrahydro-3-furanyl acetate		C₁₃H₁₈O₉	详情	详情
(II)	33827	methyl 1H-1,2,4-triazole-3-carboxylate	4928-88-5	C₄H₅N₃O₂	详情	详情
(III)	60539	methyl 1-{(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-[(acetyloxy)methyl]tetrahydro-2-furanyl}-1H-1,2,4-triazole-3-carboxylate		C₁₅H₁₉N₃O₉	详情	详情
(IV)	60540	methyl 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-1H-1,2,4-triazole-3-carboxylate		C₉H₁₃N₃O₆	详情	详情

Extended Information