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

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

Research output: Contribution to journal › Article

27 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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Alcohols
Catalysts
Acids
montmorillonite K-10
olivose

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Novel stereocontrolled glycosidations of olivoses using montmorillonite K-10 as an environmentally benign catalyst. / Jyojima, Takaaki; Miyamoto, Naoki; Ogawa, Yasumasa; Matsumura, Shuichi; Toshima, Kazunobu.

In: Tetrahedron Letters, Vol. 40, No. 27, 02.07.1999, p. 5023-5026.

Research output: Contribution to journal › Article

Jyojima, T, Miyamoto, N, Ogawa, Y, Matsumura, S & Toshima, K 1999, 'Novel stereocontrolled glycosidations of olivoses using montmorillonite K-10 as an environmentally benign catalyst', Tetrahedron Letters, vol. 40, no. 27, pp. 5023-5026. https://doi.org/10.1016/S0040-4039(99)00924-7
Jyojima T, Miyamoto N, Ogawa Y, Matsumura S, Toshima K. Novel stereocontrolled glycosidations of olivoses using montmorillonite K-10 as an environmentally benign catalyst. Tetrahedron Letters. 1999 Jul 2;40(27):5023-5026. https://doi.org/10.1016/S0040-4039(99)00924-7
Jyojima, Takaaki ; Miyamoto, Naoki ; Ogawa, Yasumasa ; Matsumura, Shuichi ; Toshima, Kazunobu. / Novel stereocontrolled glycosidations of olivoses using montmorillonite K-10 as an environmentally benign catalyst. In: Tetrahedron Letters. 1999 ; Vol. 40, No. 27. pp. 5023-5026.
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