Stereoselective Synthesis of Novel N-β-Glycosyl Sulfonamides by Sulfonamidoglycosylation of Per-O-acetylated Sugars

Abstract

A series of novel N-glycosyl sulfonamides is prepared by sulfonamidoglycosylation of per-O-acetylated sugars. The products which contain an unnatural sulfonamide moiety at the anomeric centre are obtained in very good yields and with excellent β-stereoselectivity, even with per-O-acetylated d-mannose.

Key words

sulfonamidoglycosylation - per-O-acetylated carbohydrates - sulfonamides - β-stereoselectivity - exo-anomeric effect

References

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11

de Bravo, M. G. [INIBIOLP (UNLP-CONICET), Fac. Cs. Médicas] personal communication.

18

^¹H and ^¹³C NMR spectra of the crude reaction mixtures showed only the presence of β-sulfonamidomanno-pyranoside and unreacted per-O-acetylated manno-pyranoside.