Triazole and Imidazole Reversed Nucleosides of L-Idose and D-Glucose

Abstract

6-azido-6-deoxy-gluco-(galacto)pyranose and 5-azido-5-deoxy-glucofuranose derivatives were used to obtain reversed nucleoside analogues with either the 5-aminoimidazole-4-carboxamide or 5-amino-1,2,3-triazol-4-carboxamide groups attached, through the N-1 site, to the C-6′ (C-5′) site of the sugar. When deprotected some of these compounds cyclised spontaneously to form a bond between the exocylic nitrogen and the anomeric carbon of the sugar.