AZIDO-PHENYLSELENYLATION OF -ISOPROPYLIDENE-D-ARABINO-1,4-ANHYDRO-HEX-1-ENITOL - CONVENIENT PREPARATION OF 2-AZIDO-2-DEOXY-D-GLUCOFURANO-DONOR AND GLUCOPYRANOSIDE DONORS

Azido-phenylselenylation of O-benzyl-2-deoxy-5,6-O-isopropylidene-D-ar abino-1, 4-anhydrohex-1-enitol (1) afforded an alpha/beta mixture of p henyl xy-5,6-O-isopropylidene-1-seleno-D-glucofuranoside (2) together with a small amount of -O-isopropylidene-2-phenylseleno-D-glucofur?ano syl azide (3). Acetolysis of the mixture afforded 2-azido-2-deoxy-gluc ofuranosyl donor (4). Hydrolysis of the acetal group and of the seleno glycoside 2 followed by acetylation and removal of the anomeric acetat e provide an efficient access to -acetyl-2-azido-3-O-benzyl-2-deoxy-D- glucopyranose (8), synthetic equivalent of D-glucosamine.