Abstract
Tetra-O-benzylglucose 1 and trichloroacetonitrile afford in a base catalyzed, fast, and reversible reaction the β-O-glycosyl imidate 3-β, which is transformed slowly into the α-isomer 3-α. Both results, the reactivity differences of 2α,β and the stability differences of 3-α/β are due to lone pair repulsions implicated in the anomeric effect.
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