Regioselective C-3-O-acylation and O-alkylation of 4,6-O-benzylidene-β-D-glucopyranoside derivatives displaying a range of anomeric substituents

Article abstract of DOI:10.1016/S0040-4039(99)01420-3

Regioselective C-3-O-acylation and O-alkylation of ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside, phenyl 4,6-O-benzylidene-β-D-glucopyranoside and phenyl 4,6-O-benzylidene-1-seleno-β-D-glucopyranoside is described. Regioselectivity is obtained by first treating the benzylidene diols with sodium hydride and copper (II) chloride to form a THF soluble copper chelate.