6-Azido-3-O-benzyl-6-deoxy-N,N-diethyl-1,2-O-isopropylidene-d-glycero-α-d-gluco-heptofuranuronamide

Abstract

Reaction of 3-O-benzyl-1,2-O-isopropylidene-α-xylo-pentodialdo-1,4-furanose with N,N-diethyl-2-(dimethylsulfuranilidene)acetamide gave stereoselectively an epoxyamide, which was regioselectively opened by NaN3 in dimethyl formamide to give the title compound, C21H30N4O6. X-ray crystallography confirmed the relative stereochemistry of the title compound and the absolute configuration was determined by the use of d-glucose as the starting material. There are two molecules in the asymmetric unit (Z′ = 2). The crystal structure consists of two types of chains of O—H...O hydrogen-bonded molecules running parallel to the b axis, with each molecule acting as a donor and acceptor of one hydrogen bond.