Selective formation of C-2 azidodeoxy-d-glucose derivatives from d-glucal precursors using the azidonitration reaction Original Research Article

A series of glucals, protected by cyclic acetal protecting groups to conformationally constrain the C-4 and C-6 hydroxyl groups, were subjected to the azidonitration reaction to furnish the corresponding C-2 azidodeoxy-d-glucoses. 4,6-O-Isopropylidene-3-O-triisopropylsilyl-d-arabino-hex-1-enitol afforded 2-azido-2-deoxy-4,6-O-isopropylidene-3-O-triisopropylsilyl-d-glucopyranosyl nitrate and its d-manno isomer in a 20:1 ratio. These findings allow the azidonitration reaction to be now used for the preparation of a variety of glucosamine building blocks from differentially protected glucal precursors.