The reaction of N-dichloromethylene-N,N-dimethylammonium chloride (Viehe's salt) with methyl 4,6-O-benzylidene-α-D-glucoside. An alternative synthesis of methyl 4,6-O-benzylidene-α-D-alloside

Abstract

The reaction of methyl 4,6-O-benzylidene-α-D-glucoside with N-dichloromethylene-N,N-dimethyl-ammonium chloride (Viehe's salt) in the presence of a base gives a mixture of carbamates (with triethylamine) or the 2,3-carbonate mainly (with pyridine). The treatment of this carbonate with various primary and secondary amines, again to give mixtures of carbamates, and an efficient synthesis of methyl 4,6-O-benzylidene-α-D-alloside from one of the gluco carbamates, are reported.