Glycosyl fluorides in glycosidations

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. (C) 2000 Elsevier Science Ltd.