A Regioselective Synthesis of Genistein 4’-O-Ribofuranosides

Abstract

A direct glycosylation reaction of biologically significant isoflavone, genistein (1) with 1,2,3,5-tetra-O-acetyl-β-d-ribofuranose (2) in the presence of tin tetrachloride gave a satisfactory yield of a mixture of 4’-O-α- (3a) and 4’-O-β-d-ribofuranosides (3b), in the ratio 1:2 respectively. After deacetylation, anomers 4a and 4b were separated by chromatographic means. The results are compared with ribosylation of phenol and the regio- and stereoselectivity of genistein glycosylation are discussed.

Key words

bioorganic chemistry - isoflavones - genistein O-glycosides - O-ribosylation - regioselectivity of glycosylation

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