Reaction of Peracylated Sugars with Nitriles Catalyzed by Lewis Acids

Abstract

The reaction of acetylaminoacetonitrile with penta-O-benzoyl-α-D-glucopyranose in dichloromethane-nitromethane, in a 1:1 stoichiometric proportion, catalysed by stannic chloride, gave a nitrilium salt that, after hydrolysis, afforded the corresponding N-acyl glycosylamine and a mixture of several compounds originating from different competitive reactions. Among these compounds, N-benzoyl-3,5,6-tri-O-benzoyl-β-D-glucofuranosyl amine, tetra-O-benzoyl-D-glucopyranose, and octa-O-benzoyl-β-D-glucopyranosyl-(1→1)-α-D-glucopyranoside (octa-O-benzoyl-α,β-trehalose) were identified.