GM-160575
Chemical Name: (1R,3aR,4S,4aR,7R,7aR,8aS)-8a-(6-Deoxy-4-O-methyl-3-O-octanoyl-beta-D-altropyranosyloxymethyl)-4-formyl-3-isopropyl-7-methyl-1,3a,4,4a,5,6,7,7a,8,8a-decahydro-1,4-methano-s-indacene-3a-carboxylic acid
CAS No. 179052-04-1
项目整合开发状态: Biological Testing
项目研究机构: GlaxoSmithKline (Originator)
合成路线:Sordarin (I) was isolated from culture broths of Sordaria araneosa.Protection of the carboxyl group of (I) as the benzhydryl ester (II) was effected by treatment with diphenyl diazomethane.The 2'-hydroxyl group of (II) was subsequently blocked as the carbonate ester (III) by selective acylation with benzyl chloroformate in the presence of DMAP.Subsequent esterification of the 3'-hydroxyl of (III) with octanoyl chloride (IV) furnished the octanoate ester (V).The benzhydryl ester and benzyl carbonate protecting groups of (V) were finally removed by catalytic hydrogenation over Pd/C.
📌 参考资料/链接：
参考文献标题:Antifungal sordarin derivs.
文献作者:Hayes,M.; Wildman,H.; Dawson,M.; Chalk,P.; Hall,R.; Ruiz Gomez,J.R.(GlaxoSmithKline plc)
参考来源:EP 0711783; EP 0791007; JP 1999502188; US 6054478; WO 9614327
📄 详细内容
合成路线:Sordarin (I) was isolated from culture broths of Sordaria araneosa.Protection of the carboxyl group of (I) as the benzhydryl ester (II) was effected by treatment with diphenyl diazomethane.The 2'-hydroxyl group of (II) was subsequently blocked as the carbonate ester (III) by selective acylation with benzyl chloroformate in the presence of DMAP.Subsequent esterification of the 3'-hydroxyl of (III) with octanoyl chloride (IV) furnished the octanoate ester (V).The benzhydryl ester and benzyl carbonate protecting groups of (V) were finally removed by catalytic hydrogenation over Pd/C.
参考文献标题:Antifungal sordarins.Synthesis and structure-activity relationships of 3'-O-substituted derivatives
文献作者:Arribas,E.M.; Castro,J.; Clemens,I.R.; Cuevas,J.C.; Chicharro,J.; Fraile,M.T.; Garc韆-Ochoa,S.; G髆ez de las Heras,F.; Ruiz,J.R.
参考来源:Bioorg Med Chem Lett 2002,12(2),117