A novel greener glycosidation using an acid-ionic liquid containing a protic acid

Kaname Sasaki; Hideyuki Nagai; Shuichi Matsumura; Kazunobu Toshima

doi:10.1016/S0040-4039(03)01376-5

A novel greener glycosidation using an acid-ionic liquid containing a protic acid

Kaname Sasaki, Hideyuki Nagai, Shuichi Matsumura, Kazunobu Toshima

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

61 Citations (Scopus)

Abstract

The glycosidations of glucopyranosyl diethyl phosphite and alcohols using an ionic liquid, 1-n-hexyl-3-methylimidazolium trifluoromethanesulfonimidide (C₆mim[NTf₂]) containing a protic acid, trifluoromethanesulfonimide (HNTf₂), as a novel solvent-catalyst system, effectively proceeded under mild conditions to give the corresponding glycosides in good to high yields. Furthermore, this acid-ionic liquid combination could be reused many times for the glycosidations without any loss in efficiency.

Original language	English
Pages (from-to)	5605-5608
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	30
DOIs	https://doi.org/10.1016/S0040-4039(03)01376-5
Publication status	Published - 2003 Jul 21

Keywords

Diethyl phosphite
Glycosidation
Green chemistry
Ionic liquid
Protic acid

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(03)01376-5

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title = "A novel greener glycosidation using an acid-ionic liquid containing a protic acid",

abstract = "The glycosidations of glucopyranosyl diethyl phosphite and alcohols using an ionic liquid, 1-n-hexyl-3-methylimidazolium trifluoromethanesulfonimidide (C6mim[NTf2]) containing a protic acid, trifluoromethanesulfonimide (HNTf2), as a novel solvent-catalyst system, effectively proceeded under mild conditions to give the corresponding glycosides in good to high yields. Furthermore, this acid-ionic liquid combination could be reused many times for the glycosidations without any loss in efficiency.",

keywords = "Diethyl phosphite, Glycosidation, Green chemistry, Ionic liquid, Protic acid",

author = "Kaname Sasaki and Hideyuki Nagai and Shuichi Matsumura and Kazunobu Toshima",

note = "Funding Information: We sincerely thank Dr. Y. Katayama and Mr. M. Yamagata for their helpful discussions. This research was partially supported by Grant-in-Aid for the 21st Century COE program {\textquoteleft}KEIO Life Conjugate Chemistry{\textquoteright} from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.",

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T1 - A novel greener glycosidation using an acid-ionic liquid containing a protic acid

AU - Sasaki, Kaname

AU - Nagai, Hideyuki

AU - Matsumura, Shuichi

AU - Toshima, Kazunobu

N1 - Funding Information: We sincerely thank Dr. Y. Katayama and Mr. M. Yamagata for their helpful discussions. This research was partially supported by Grant-in-Aid for the 21st Century COE program ‘KEIO Life Conjugate Chemistry’ from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.

PY - 2003/7/21

Y1 - 2003/7/21

N2 - The glycosidations of glucopyranosyl diethyl phosphite and alcohols using an ionic liquid, 1-n-hexyl-3-methylimidazolium trifluoromethanesulfonimidide (C6mim[NTf2]) containing a protic acid, trifluoromethanesulfonimide (HNTf2), as a novel solvent-catalyst system, effectively proceeded under mild conditions to give the corresponding glycosides in good to high yields. Furthermore, this acid-ionic liquid combination could be reused many times for the glycosidations without any loss in efficiency.

AB - The glycosidations of glucopyranosyl diethyl phosphite and alcohols using an ionic liquid, 1-n-hexyl-3-methylimidazolium trifluoromethanesulfonimidide (C6mim[NTf2]) containing a protic acid, trifluoromethanesulfonimide (HNTf2), as a novel solvent-catalyst system, effectively proceeded under mild conditions to give the corresponding glycosides in good to high yields. Furthermore, this acid-ionic liquid combination could be reused many times for the glycosidations without any loss in efficiency.

KW - Diethyl phosphite

KW - Glycosidation

KW - Green chemistry

KW - Ionic liquid

KW - Protic acid

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JO - Tetrahedron Letters

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A novel greener glycosidation using an acid-ionic liquid containing a protic acid

Abstract

Keywords

ASJC Scopus subject areas

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