Novel stereocontrolled glycosidations of olivoses using montmorillonite K-10 as an environmentally benign catalyst

Takaaki Jyojima, Naoki Miyamoto, Yasumasa Ogawa, Shuichi Matsumura, Kazunobu Toshima

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28 Citations (Scopus)

Abstract

Novel stereocontrolled glycosidations of 3,4-di-O-protected olivoses and alcohols using a heterogeneous and environmentally benign solid acid, montmorillonite K-10, have been developed. The glycosidations of the 3-O-Ac- 4-O-TBS-olivose (4) and various alcohols using montmorillonite K-10 in CH2CI2 at 25 °C exclusively gave the corresponding α-olivosides in high yields. On the other hand, the corresponding β-olivosides were predominately obtained by the glycosidations of the 3-O-TBS-4-O-Ac-olivose (5) and various alcohols under similar conditions.

Original languageEnglish
Pages (from-to)5023-5026
Number of pages4
JournalTetrahedron Letters
Volume40
Issue number27
DOIs
Publication statusPublished - 1999 Jul 2

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Keywords

  • Environmentally benign synthesis
  • Glycosidation
  • Montmofillonite K-10
  • Olivose
  • Olivoside

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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