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

研究成果: Article

44 引用 (Scopus)

抜粋

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.

元の言語English
ページ(範囲)5331-5339
ページ数9
ジャーナルTetrahedron
60
発行部数25
DOI
出版物ステータスPublished - 2004 6 14

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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