Glycosyl fluorides in glycosidations Review Article

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 SnCl2AgClO4, SnCl2TrClO4, SnCl2AgOTf, TMSOTf, SiF4, BF3·Et2O, TiF4, SnF4, Cp2MCl2AgClO4 (M=Zr or Hf), Cp2ZrCl2AgBF4, Cp2HfCl2AgOTf, Bu2Sn(ClO4)2, Me2GaCl, Tf2O, LiClO4, Yb(OTf)3, La(ClO4)3·nH2O, La(ClO4)3·nH2OSn(OTf)2, YbAmberlyst 15, SO4/ZrO2, Nafion-H®, montmorillonite K-10, and TrB(C6F5)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.