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

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Stereoselectivity
Fluorides
Alcohols
Acids
zirconium oxide

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Stereocontrolled glycosidations using a heterogeneous solid acid, sulfated zirconia, for the direct syntheses of α- and β-manno- and 2-deoxyglucopyranosides. / Toshima, Kazunobu; Nagai, Hideyuki; Kasumi, Ken Ichi; Kawahara, Kanako; Matsumura, Shuichi.

In: Tetrahedron, Vol. 60, No. 25, 14.06.2004, p. 5331-5339.

Research output: Contribution to journalArticle

Toshima, Kazunobu ; Nagai, Hideyuki ; Kasumi, Ken Ichi ; Kawahara, Kanako ; Matsumura, Shuichi. / Stereocontrolled glycosidations using a heterogeneous solid acid, sulfated zirconia, for the direct syntheses of α- and β-manno- and 2-deoxyglucopyranosides. In: Tetrahedron. 2004 ; Vol. 60, No. 25. pp. 5331-5339.
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