Glycosyl fluorides in glycosidations

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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 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.

Original languageEnglish
Pages (from-to)15-26
Number of pages12
JournalCarbohydrate Research
Volume327
Issue number1-2
DOIs
Publication statusPublished - 2000 Jul 10

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Keywords

  • C- Glycoside
  • C-Glycosidation
  • Glycosyl fluoride
  • O-Glycosidation
  • O-Glycoside

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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