Aryl C-glycosylation using an ionic liquid containing a protic acid

Chigusa Yamada; Kaname Sasaki; Shuichi Matsumura; Kazunobu Toshima

doi:10.1016/j.tetlet.2007.04.077

Aryl C-glycosylation using an ionic liquid containing a protic acid

Chigusa Yamada, Kaname Sasaki, Shuichi Matsumura, Kazunobu Toshima

Department of Applied Chemistry

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

16 Citations (Scopus)

Abstract

Aryl C-glycosylation of several glycosyl donors, including unprotected sugars, with phenol and naphthol derivatives in an ionic liquid containing a protic acid proceeded effectively and stereoselectively to give the corresponding aryl C-glycosides in good to high yields. Because the ionic liquid was nonvolatile, the reaction could be carried out under reduced pressure; in addition, the ionic liquid could be reused without loss of effectiveness. These features contribute to the significant advantages of this novel aryl C-glycosylation reaction.

Original language	English
Pages (from-to)	4223-4227
Number of pages	5
Journal	Tetrahedron Letters
Volume	48
Issue number	24
DOIs	https://doi.org/10.1016/j.tetlet.2007.04.077
Publication status	Published - 2007 Jun 11

Keywords

Aryl C-glycosylation
Carbohydrate
Ionic liquid
Protic acid

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2007.04.077

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title = "Aryl C-glycosylation using an ionic liquid containing a protic acid",

abstract = "Aryl C-glycosylation of several glycosyl donors, including unprotected sugars, with phenol and naphthol derivatives in an ionic liquid containing a protic acid proceeded effectively and stereoselectively to give the corresponding aryl C-glycosides in good to high yields. Because the ionic liquid was nonvolatile, the reaction could be carried out under reduced pressure; in addition, the ionic liquid could be reused without loss of effectiveness. These features contribute to the significant advantages of this novel aryl C-glycosylation reaction.",

keywords = "Aryl C-glycosylation, Carbohydrate, Ionic liquid, Protic acid",

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

note = "Funding Information: This research was supported in part by a Grant-in-Aid for the 21st Century COE Program {\textquoteleft}KEIO Life Conjugated Chemistry{\textquoteright}, for Scientific Research on Priority Areas 18032068, and for JSPS Fellows 18·6013 from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.",

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month = jun,

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doi = "10.1016/j.tetlet.2007.04.077",

language = "English",

volume = "48",

pages = "4223--4227",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Aryl C-glycosylation using an ionic liquid containing a protic acid

AU - Yamada, Chigusa

AU - Sasaki, Kaname

AU - Matsumura, Shuichi

AU - Toshima, Kazunobu

N1 - Funding Information: This research was supported in part by a Grant-in-Aid for the 21st Century COE Program ‘KEIO Life Conjugated Chemistry’, for Scientific Research on Priority Areas 18032068, and for JSPS Fellows 18·6013 from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.

PY - 2007/6/11

Y1 - 2007/6/11

N2 - Aryl C-glycosylation of several glycosyl donors, including unprotected sugars, with phenol and naphthol derivatives in an ionic liquid containing a protic acid proceeded effectively and stereoselectively to give the corresponding aryl C-glycosides in good to high yields. Because the ionic liquid was nonvolatile, the reaction could be carried out under reduced pressure; in addition, the ionic liquid could be reused without loss of effectiveness. These features contribute to the significant advantages of this novel aryl C-glycosylation reaction.

AB - Aryl C-glycosylation of several glycosyl donors, including unprotected sugars, with phenol and naphthol derivatives in an ionic liquid containing a protic acid proceeded effectively and stereoselectively to give the corresponding aryl C-glycosides in good to high yields. Because the ionic liquid was nonvolatile, the reaction could be carried out under reduced pressure; in addition, the ionic liquid could be reused without loss of effectiveness. These features contribute to the significant advantages of this novel aryl C-glycosylation reaction.

KW - Aryl C-glycosylation

KW - Carbohydrate

KW - Ionic liquid

KW - Protic acid

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DO - 10.1016/j.tetlet.2007.04.077

M3 - Article

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SN - 0040-4039

VL - 48

SP - 4223

EP - 4227

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 24

ER -

Aryl C-glycosylation using an ionic liquid containing a protic acid

Abstract

Keywords

ASJC Scopus subject areas

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