Glycosyl fluorides in glycosidations

Abstract

This short review deals with the recent progress in chemical O-glycosidation and C-glycosylation methods using glycosyl fluorides as glycosyl donors. Pyranosyl and furanosyl fluorides were effectively activated by fluorophilic reagents such as SnCl 2AgClO 4, SnCl 2TrClO 4, SnCl 2AgOTf, TMSOTf, SiF 4, BF 3·Et 2O, TiF 4, SnF 4, Cp 2MCl 2AgClO 4 (M=Zr or Hf), Cp 2ZrCl 2AgBF 4, Cp 2HfCl 2AgOTf, Bu 2Sn(ClO 4) 2, Me 2GaCl, Tf 2O, LiClO 4, Yb(OTf) 3, La(ClO 4) 3· nH 2O, La(ClO 4) 3· nH 2OSn(OTf) 2, YbAmberlyst 15, SO 4/ZrO 2, Nafion-H ®, montmorillonite K-10, and TrB(C 6F 5) 4 to react with alcohols to give the corresponding O-glycosides in high yields. Furthermore, several types of C-glycosides, such as aryl, allyl and alkyl C-glycosyl derivatives, were also obtained by the glycosylation using glycosyl fluorides and the corresponding nucleophile with or without a Lewis acid.