A Convenient Synthesis of Pyranosyl-1-carbaldoximes

A simple high-yielding procedure is described for the preparation of tri-O-acetyl-beta-L-fucopyranosylformaldoxime (1) involving stannate(II)-mediated reduction of the readily accessible tri-O-acetyl-beta-L-fucopyranosylnitromethane (3). The D-mannosyl, D-glucosyl, D-galactosyl, and D-xylosyl analogues 7-12 were prepared similarly. The structure of tetra-O-acetyl-beta-D-mannopyranosylformaldoxime (7) was determined by X-ray crystallography.