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

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

doi:10.1016/S0040-4039(99)00924-7

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

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

Department of Applied Chemistry

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	5023-5026
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	27
DOIs	https://doi.org/10.1016/S0040-4039(99)00924-7
Publication status	Published - 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

Cite this

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, 40(27), 5023-5026. https://doi.org/10.1016/S0040-4039(99)00924-7

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AU - Toshima, Kazunobu

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10.1016/S0040-4039(99)00924-7