REACTION OF ORGANOCUPRATE REAGENTS WITH PROTECTED 1,2-ANHYDRO SUGARS - STEREOCONTROLLED SYNTHESIS OF 2-DEOXY-C-GLYCOSYL COMPOUNDS

The reaction of protected 1,2-anhydro-alpha-D-gluco- and beta-D-manno- pyranoses with alkyl and phenyl organocuprates afforded the correspond ing C-glycosyl compounds in acceptable to high yield. Complete stereoc ontrol was obtained, leading respectively to the beta-D or the alpha-D anomer. With the perbenzylated manno derivative, deoxygenation at C-2 was achieved in high yield, affording 2-deoxy-alpha-D-C-glycosyl comp ounds.