Nitrogen-containing carbohydrate derivatives. Part XXIII. Some ring-opening reactions of methyl 2,3-N-aroylepimino-4,6-O-benzylidene-2,3-dideoxy-α-D-mannopyranosides

Abstract

Reaction of methyl 2,3-N-aroylepimino-4,6-O-benzylidene-α-D-mannosides (1) with sodium iodide in NN-dimethylformamide gave only the 2-N-3-O-oxazolines. Reaction with thiocyanate ion, however, gave no oxazolines but instead the methyl 2-arylamido-4,6-O-benzylidene-3-deoxy-3-thiocyanato-α-D-altrosides, which were desulphurised to give the appropriate 2,3-dideoxy-2-arylamido-derivatives.