Glycosyl fluorides in glycosidations

This short review deals with the recent progress in chemical O-glycosidatio n and C-glycosylation methods using glycosyl fluorides as glycosyl donors. Pyranosyl and furanosyl fluorides were effectively activated by fluorophili c reagents such as SnCl2-AgClO4, SnCl2-TrClO4, SnCl2-AgOTf, TMSOTf, SiF4, B F3.Et2O, TiF4, SnF4, Cp2MCl2-AgClO4 (M = Zr or Hf), Cp2ZrCl2-AgBF4, Cp2HfCl 2-AgOTf, Bu2Sn(ClO4)(2), Me2GaCl, Tf2O, LiClO4, Yb(OTf)(3), La(ClO4)(3).nH( 2)O, La(ClO4)(3).n H2O-Sn(OTf)(2), Yb-Amberlyst 15, SO4/ZrO2, Nafion-H(R), montmorillonite K-10, and TrB(C6F5)(4) to react with alcohols to give the c orresponding O-glycosides in high yields. Furthermore, several types of C-g lycosyl compounds, such as aryl, allyl and alkyl C-glycosyl derivatives, we re also obtained by the glycosylation using glycosyl fluorides and the corr esponding nucleophile with or without a Lewis acid. (C) 2000 Elsevier Scien ce Ltd. All rights reserved.