Efficient and stereoselective glycosylation remains one of challenging endeavors in organic synthesis. This holds especially true in cases such as �-linked deoxy-sugars, where the outcome of the glycosylation cannot be controlled using the stereochemical information intrinsic to the glycosyl donor. We show that sulfonic anhydrides activate deoxy-sugar hemiacetals as electrophiles which react stereoselectively with nucleophilic acceptors to produce �-anomers exclusively.NMR studies support this finding, indicating that the hemiacetal is quantitatively converted into an a-glycosyl tosylate, presumably the reactive species in the reaction. This approach demonstrates the viability of a more general reagent-controlled activation protocol which is centered around matching sulfonate reactivity with donor reactivity to effect highly stereoselective glycosylation through an SN2-like reaction manifold.

Reagent-controlled S<sub>N</sub>2-glycosylation for the direct synthesis of �-linked 2-deoxy-sugars

248th National Meeting (2014)

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Reagent-controlled SN2-glycosylation for the direct synthesis of �-linked 2-deoxy-sugars

Reagent-controlled S_N2-glycosylation for the direct synthesis of �-linked 2-deoxy-sugars