Effective synthesis of 7-hydroxyisoflavone O-glucosides

An effective procedure for condensing acetobromoglucose with 2,4-dihydroxy-phenyl benzyl ketones has been developed. The 2-hydroxy-4-(-D-tetra-O-acetylglucopyranosyloxy)phenyl benzyl ketones synthesized with yields of 47–69% have been converted under the action of ethyl orthoformate in pyridine solution into 7-hydroxyisoflavone O-glucosides and these have also been obtained by the glycosylation of 7-hydroxyisoflavone. The advantages and disadvantages of the alternative pathways of the synthesis of 7-hydroxyisoflavone O-glycosides are discussed.T. G. Shevchenko Kiev State University. Khar'kov State Pharmaceutical Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 511–519, July–August, 1988.