A novel glycosidation of glycosyl fluoride using a designed ionic liquid and its effect on the stereoselectivity

Kaname Sasaki; Shuichi Matsumura; Kazunobu Toshima

doi:10.1016/j.tetlet.2004.07.128

A novel glycosidation of glycosyl fluoride using a designed ionic liquid and its effect on the stereoselectivity

Kaname Sasaki, Shuichi Matsumura, Kazunobu Toshima

Department of Applied Chemistry

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

40 Citations (Scopus)

Abstract

The glycosidations of glucopyranosyl fluoride and alcohols using an ionic liquid containing a protic acid effectively proceeded under mild conditions to afford the corresponding glycosides in good to high yields. The stereoselectivity of the glycosidation was significantly affected by the ionic liquid solvent. 1-n-Hexyl-3-methylimidazolium trifluoromethanesulfonate (C ₆mim[OTf]), containing a trifluoromethanesulfonate anion, and 1-(3-cyanopropyl)-3-methylimidazolium trifluoromethanesulfonimidide (CNC ₃mim[NTf ₂]), possessing a cyano group at the side chain of the imidazolium cation, gave the β-stereoselectivity.

Original language	English
Pages (from-to)	7043-7047
Number of pages	5
Journal	Tetrahedron Letters
Volume	45
Issue number	38
DOIs	https://doi.org/10.1016/j.tetlet.2004.07.128
Publication status	Published - 2004 Sept 13

Keywords

Carbohydrate
Designability
Glycosidation
Glycosyl fluoride
Ionic liquid

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2004.07.128

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@article{50e93b6988bf4ce1992c55530811c850,

title = "A novel glycosidation of glycosyl fluoride using a designed ionic liquid and its effect on the stereoselectivity",

abstract = "The glycosidations of glucopyranosyl fluoride and alcohols using an ionic liquid containing a protic acid effectively proceeded under mild conditions to afford the corresponding glycosides in good to high yields. The stereoselectivity of the glycosidation was significantly affected by the ionic liquid solvent. 1-n-Hexyl-3-methylimidazolium trifluoromethanesulfonate (C 6mim[OTf]), containing a trifluoromethanesulfonate anion, and 1-(3-cyanopropyl)-3-methylimidazolium trifluoromethanesulfonimidide (CNC 3mim[NTf 2]), possessing a cyano group at the side chain of the imidazolium cation, gave the β-stereoselectivity.",

keywords = "Carbohydrate, Designability, Glycosidation, Glycosyl fluoride, Ionic liquid",

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

note = "Funding Information: This research was supported in part 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.",

year = "2004",

month = sep,

day = "13",

doi = "10.1016/j.tetlet.2004.07.128",

language = "English",

volume = "45",

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journal = "Tetrahedron Letters",

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number = "38",

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T1 - A novel glycosidation of glycosyl fluoride using a designed ionic liquid and its effect on the stereoselectivity

AU - Sasaki, Kaname

AU - Matsumura, Shuichi

AU - Toshima, Kazunobu

N1 - Funding Information: This research was supported in part 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 - 2004/9/13

Y1 - 2004/9/13

N2 - The glycosidations of glucopyranosyl fluoride and alcohols using an ionic liquid containing a protic acid effectively proceeded under mild conditions to afford the corresponding glycosides in good to high yields. The stereoselectivity of the glycosidation was significantly affected by the ionic liquid solvent. 1-n-Hexyl-3-methylimidazolium trifluoromethanesulfonate (C 6mim[OTf]), containing a trifluoromethanesulfonate anion, and 1-(3-cyanopropyl)-3-methylimidazolium trifluoromethanesulfonimidide (CNC 3mim[NTf 2]), possessing a cyano group at the side chain of the imidazolium cation, gave the β-stereoselectivity.

AB - The glycosidations of glucopyranosyl fluoride and alcohols using an ionic liquid containing a protic acid effectively proceeded under mild conditions to afford the corresponding glycosides in good to high yields. The stereoselectivity of the glycosidation was significantly affected by the ionic liquid solvent. 1-n-Hexyl-3-methylimidazolium trifluoromethanesulfonate (C 6mim[OTf]), containing a trifluoromethanesulfonate anion, and 1-(3-cyanopropyl)-3-methylimidazolium trifluoromethanesulfonimidide (CNC 3mim[NTf 2]), possessing a cyano group at the side chain of the imidazolium cation, gave the β-stereoselectivity.

KW - Carbohydrate

KW - Designability

KW - Glycosidation

KW - Glycosyl fluoride

KW - Ionic liquid

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U2 - 10.1016/j.tetlet.2004.07.128

DO - 10.1016/j.tetlet.2004.07.128

M3 - Article

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SN - 0040-4039

VL - 45

SP - 7043

EP - 7047

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 38

ER -

A novel glycosidation of glycosyl fluoride using a designed ionic liquid and its effect on the stereoselectivity

Abstract

Keywords

ASJC Scopus subject areas

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