新产品编号:1204411

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合成路线:Treatment of L-lyxose (I) with MeOH and H2SO4 afforded a 1:3 mixture of 1-O-methyl lyxopyranose (II) and 1-O-methyl lyxofuranose (III).This mixture was treated with CuSO4 and H2SO4 in acetone to give a mixture of 2,3- (IV) and 3,5- (V) isopropylidene acetals,together with some of the pyranose isomer,which was removed by silica gel chromatography.Selective tosylation of the primary hydroxyl group by treatment with p-toluenesulfonyl chloride and pyridine afforded,after chromatographic separation,tosylate (VI).Subsequent reduction with LiAlH4 in refluxing Et2O/toluene at reflux provided 5-deoxy compound (VII).Then,concomitant deprotection and acetylation with AcOH and Ac2O yielded triacetate (VIII) as a mixture of anomers.Condensation with silyl benzimidazole (IX),(obtained in situ by treatment of 2-bromo-5,6-dichlorobenzimidazole with bis(trimethylsilyl)acetamide in acetonitrile),in the presence of trimethylsilyl triflate produced the glycosylated benzimidazole (X).Finally,acetate groups were hydrolyzed by treatment with Na2CO3 in a hydroalcoholic mixture.