Azido-Phenylselenylation of 3-O-Benzyl-2-Deoxy-5,6-O-Isopropylidene-D-Arabino-1,4-Anhydro-Hex-1-Enitol: Convenient Preparation of 2-Azido-2-Deoxy-D-Glucofurano-and Glucopyranoside Donors.

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Abstract
Azido-phenylselenylation of 3-O-benzyl-2-deoxy-5,6-O-isopropylidene-D-arabino-1,4-anhydrohex-1-enitol (1) afforded an α/β mixture of phenyl 2-azido-3-O-benzyl-2-deoxy-5,6-O-isopropylidene-1-seleno-D-glucofuranoside (2) together with a small amount of 3-O-benzyl-2-deoxy-5,6-O-isopropylidene-2-phenylseleno-D-glucofuranosyl azide (3). Acetolysis of the mixture afforded 2-azido-2-deoxyglucofuranosyl donor (4). Hydrolysis of the acetal group and of the selenoglycoside 2 followed by acetylation and removal of the anomeric acetate provide an efficient access to 5,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-D-glucopyranose (8), synthetic equivalent of D-glucosamine.