A novel glycosidation of glycosyl fluoride using a designed ionic liquid and its effect on the stereoselectivity

Kaname Sasaki, Shuichi Matsumura, Kazunobu Toshima

Research output: Contribution to journalArticlepeer-review

52 Citations (Scopus)

Abstract

The glycosidations of glucopyranosyl fluoride and alcohols using an ionic liquid containing a protic acid effectively proceeded under mild conditions to afford the corresponding glycosides in good to high yields. The stereoselectivity of the glycosidation was significantly affected by the ionic liquid solvent. 1-n-Hexyl-3-methylimidazolium trifluoromethanesulfonate (C 6mim[OTf]), containing a trifluoromethanesulfonate anion, and 1-(3-cyanopropyl)-3-methylimidazolium trifluoromethanesulfonimidide (CNC 3mim[NTf 2]), possessing a cyano group at the side chain of the imidazolium cation, gave the β-stereoselectivity.

Original languageEnglish
Pages (from-to)7043-7047
Number of pages5
JournalTetrahedron Letters
Volume45
Issue number38
DOIs
Publication statusPublished - 2004 Sep 13

Keywords

  • Carbohydrate
  • Designability
  • Glycosidation
  • Glycosyl fluoride
  • Ionic liquid

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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