R-1270, ICN-17261, Levovirin
左旋韦林Chemical Name: 1-(beta-L-Ribofuranosyl)-1H-1,2,4-triazole-3-carboxamide
CAS No. 206269-27-4
项目整合开发状态: Discontinued
项目研究机构: Ribapharm (Originator), Roche (Licensee)
合成路线:Treatment of L-ribose (I) with MeOH in the presence of acid catalyst gave 1-O-methyl ribofuranoside (II),which was esterified with Ac2O in pyridine to afford triacetate (III).Subsequent treatment with Ac2O and AcOH produced tetraacetyl ribofuranoside (IV).Condensation of (IV) with methyl 1,2,4-triazole-3-carboxylate (V) using a catalytic amount of bis(p-nitrophenyl)phosphate at high temperature provided the desired nucleoside (VI) along with minor amounts of its triazole regioisomer (VII),which were separated by column chromatography.Displacement of the methyl ester of (VII) with methanolic ammonia,with concomitant deprotection of the acetate esters furnished the title carboxamide.
📌 参考资料/链接：
参考文献标题:Monocyclic L-nucleosides,analogs and uses thereof
文献作者:Ramasamy,K.; Averett,D.; Tam,R.(ICN Pharmaceuticals,Inc.)
参考来源:EP 1027359; WO 9816186
📄 详细内容
合成路线:Treatment of L-ribose (I) with MeOH in the presence of acid catalyst gave 1-O-methyl ribofuranoside (II),which was esterified with Ac2O in pyridine to afford triacetate (III).Subsequent treatment with Ac2O and AcOH produced tetraacetyl ribofuranoside (IV).Condensation of (IV) with methyl 1,2,4-triazole-3-carboxylate (V) using a catalytic amount of bis(p-nitrophenyl)phosphate at high temperature provided the desired nucleoside (VI) along with minor amounts of its triazole regioisomer (VII),which were separated by column chromatography.Displacement of the methyl ester of (VII) with methanolic ammonia,with concomitant deprotection of the acetate esters furnished the title carboxamide.
参考文献标题:Monocyclic L-nucleosides with type 1 cytokine-inducing activity
文献作者:Ramasamy,K.S.; Tam,S.; Bard,J.; Averett,D.R.
参考来源:J Med Chem 2000,43(5),1019
产品链接: CAS No. 206269-27-4››