Stereocontrolled glycosidations using a heterogeneous solid acid, sulfated zirconia, for the direct syntheses of α- and β-manno- and 2-deoxyglucopyranosides

Kazunobu Toshima, Hideyuki Nagai, Ken Ichi Kasumi, Kanako Kawahara, Shuichi Matsumura

Research output: Contribution to journalArticle

44 Citations (Scopus)

Abstract

Novel α- and β-stereocontrolled glycosidations using a heterogeneous solid acid, sulfated zirconia (SO4/ZrO2), as an activator have been developed. The glycosidations of manno- and 2-deoxyglucopyranosyl α-fluorides with several alcohols using SO 4/ZrO2 in MeCN proceeded α-stereoselectively, while those with the same activator in the presence of MS 5A in Et2O occurred with β-stereoselectivity. Thus, both the α- and β-manno- and 2-deoxyglucopyranosides were effectively obtained by the present glycosidations.

Original languageEnglish
Pages (from-to)5331-5339
Number of pages9
JournalTetrahedron
Volume60
Issue number25
DOIs
Publication statusPublished - 2004 Jun 14

Keywords

  • 2-Deoxypyranoside
  • Glycosidation
  • Heterogeneous solid acid
  • Mannopyranoside
  • Sulfated zirconia

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Stereocontrolled glycosidations using a heterogeneous solid acid, sulfated zirconia, for the direct syntheses of α- and β-manno- and 2-deoxyglucopyranosides'. Together they form a unique fingerprint.

  • Cite this