Novel stereocontrolled glycosidations of 2-deoxyglucopyranosyl fluoride using a heterogeneous solid acid, sulfated zirconia (SO4[ZrO2)

Kazunobu Toshima, Ken ichi Kasumi, Shuichi Matsumura

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

Novel stereocontrolled glycosidations of a 2-deoxy-α-D-glucopyranosyl fluoride using a heterogeneous and environmentally friendly solid acid, sulfated zirconia (SO4/ZrO2), have been developed. The glycosidations of the perbenzylated 2-deoxy-α-D-glucopyranosyl fluoride 1 and various alcohols using SO4/ZrO2 in CH3CN at 25°C for 1 h predominantly gave the corresponding 2-deoxy-α-D-glucopyranosides. On the other hand, the corresponding 2-deoxy-β-D-glucopyranosides were selectively obtained by the glycosidations of 1 and various alcohols employing SO4/ZrO2 in the presence of molecular sieves 5A in Et2O at 0°C for 1 h.

Original languageEnglish
Pages (from-to)813-815
Number of pages3
JournalSynlett
Issue number6
DOIs
Publication statusPublished - 1999 Jan 1

Keywords

  • 2-deoxy sugar
  • Carbohydrate
  • Glycosidation
  • Solid acid
  • Sulfated zirconia

ASJC Scopus subject areas

  • Organic Chemistry

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