The Synthesis of Protected 5-azido-5-deoxy-D-glucononitriles as Precursors of Glycosidase Inhibitors
Bird, P., David Dolphin, and Withers, S.G.
Can J. Chem.
The successful syntheses of 5-azido-2,3,4,6-tetra-O-benzyl-5-deoxy-D-glucononitrile and 2,3,4,6-tetra-O-benzyl-5-deoxy-5-trifluoroacetamido-D-glucononitrile starting from D-glucose are described. Unsuccessful attempts were made to convert these 2 compdounds a protected 5-amino-5-deoxy-D-gluconitrile and to subsequently cyclize them to an amidine analog of glucose as a possible glycosidase inhibitor.