新产品编号:1699577

Chemical Name: 7-[6-Deoxy-4-O,5-dimethyl-3-O-(5-methyl-1H-pyrrol-2-ylcarbonyl)-alpha-L-mannopyranosyloxy]-4-[2-(1H-imidazol-2-ylsulfanyl)ethoxy]-8-methyl-2H-1-benzopyran-2-one
项目整合开发状态: Biological Testing
项目研究机构: Aventis Pharma (Originator)
合成路线:4,7-Dihydroxy-8-methylcoumarin (I) was selectively protected as the monosilylated derivative (II) using tert-butyldiphenylsilyl chloride and Et3N.Subsequent Mitsunobu coupling of (II) with 2-bromoethanol (A) produced the bromoethoxy coumarin (III).After desilylation of (III) with a mixture of HF and KF,the resulting phenol (IV) was coupled with noviose triol (V) under Mitsunobu conditions to afford the alpha-glycoside (VI) as the major isomer.Esterification of (VI) with 5-methylpyrrole-2-carboxylic anhydride (VII) in the presence of CoCl2 yielded the desired 3'-ester (VIII) along with minor amounts of 2'-ester,which was separated by column chromatography.Finally,displacement of the bromide of (VIII) by 2-mercaptoimidazole (IX) furnished the corresponding thioether.