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 › peer-review

29 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

Keywords

Environmentally benign synthesis
Glycosidation
Montmofillonite K-10
Olivose
Olivoside

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(99)00924-7

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title = "Novel stereocontrolled glycosidations of olivoses using montmorillonite K-10 as an environmentally benign catalyst",

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.",

keywords = "Environmentally benign synthesis, Glycosidation, Montmofillonite K-10, Olivose, Olivoside",

author = "Takaaki Jyojima and Naoki Miyamoto and Yasumasa Ogawa and Shuichi Matsumura and Kazunobu Toshima",

note = "Funding Information: Acknowledgment. Financial support by a Grant-in-Aid for Encouragement of Young Scientists from the Ministry of Education, Science, Sports and Culture is gratefully acknowledged.",

year = "1999",

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doi = "10.1016/S0040-4039(99)00924-7",

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T1 - Novel stereocontrolled glycosidations of olivoses using montmorillonite K-10 as an environmentally benign catalyst

AU - Jyojima, Takaaki

AU - Miyamoto, Naoki

AU - Ogawa, Yasumasa

AU - Matsumura, Shuichi

AU - Toshima, Kazunobu

N1 - Funding Information: Acknowledgment. Financial support by a Grant-in-Aid for Encouragement of Young Scientists from the Ministry of Education, Science, Sports and Culture is gratefully acknowledged.

PY - 1999/7/2

Y1 - 1999/7/2

N2 - 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.

AB - 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.

KW - Environmentally benign synthesis

KW - Glycosidation

KW - Montmofillonite K-10

KW - Olivose

KW - Olivoside

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U2 - 10.1016/S0040-4039(99)00924-7

DO - 10.1016/S0040-4039(99)00924-7

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VL - 40

SP - 5023

EP - 5026

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 27

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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