Potential affinity and photoaffinity reagents for the membrane protein of human erythrocytes involved in glucose transport. Synthesis of 6-amino-6-deoxy derivatives of D-glucose

Abstract

From 1,2-O-isopropylidene-α-D-glucofuranose 1, the 6-amino-6-deoxy-l,2:3,5-di-O-isopropylidene-α-D-glucofuranose 6 was prepared in a four-step sequence in an overall 50% yield. The conversion of 6 to the 6-bromoacetamido-6-deoxy 10, 6-deoxy-6-isothiocyanato 11, and 6-(p-azido-o-nitroanilino)-6-deoxy 12 derivatives of D-glucose is described.