Reaction of organocuprate reagents with protected 1,2-anhydro sugars. Stereocontrolled synthesis of 2-deoxy-C-glycosyl compounds

Article abstract of DOI:10.1016/0008-6215(83)85007-1

The reaction of protected 1,2-anhydro-α-D-gluco- and β-D-manno-pyranoses with alkyl and phenyl organocuprates afforded the corresponding C-glycosyl compounds in acceptable to high yield. Complete stereocontrol was obtained, leading respectively to the β-D or the α-D anomer. With the perbenzylated manno derivative, deoxygenation at C-2 was achieved in high yield, affording 2-deoxy-α-D-C-glycosyl compounds.