Synthesis and x-ray crystallographic analysis of 4,6-di-O-acetyl-2,3-dideoxy-α-d-threo-hexopyranosyl cyanide

Abstract The glycopyranosyl cyanide 4,6-di-O-acetyl-2,3-dideoxy-α- d -threo-hexopyranosyl cyanide has been synthesized from tri-O-acetyl- d -galactal by reaction with trimethylsilyl cyanide in the presence of boron trifluoride diethyl etherate followed by catalytic hydrogenation. The synthesis provides the α-anomer stereoselectively, the structure of which was assigned based on 2D NMR techniques and x-ray crystallography.