Abstract
Abstract The formation of C-C bonds at the anomeric center of carbohydrates has become an important area in organic synthesis.1 The Lewis acid catalyzed addition of carbon nucleophiles to electrophilic sugar derivatives is the most popular method generally affording α-C-glycosides in the pyranose series. Because of the kinetic anomeric effect2 of the ring oxygen, the pyran oxonium species usually accepts nucleophiles from the α-face.3 It is, however, surprising that C-glycosyl derivatives of 2-azidosugars have been scarcely reported in the literature4,5 in spite of their interest as precursors of potential inhibitors for various hexosamine transferases.
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