REACTION OF PERACYLATED SUGARS WITH NITRILES CATALYZED BY LEWIS-ACIDS

The reaction of acetylaminoacetonitrile with penta-O-benzoyl-alpha-D-g lucopyranose 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, -benzoyl-3,5,6-tri-O-benzoyl-beta-D -glucofuranosyl amine, tetra-O-benzoyl-D-glucopyranose, and octa-O-ben zoyl-beta-D-glucopyranosyl-(1-->1) -alpha-D-glucopyranoside (octa-O-be nzoyl-alpha,beta-trehalose) were identified.