Direct synthesis of 1,6-anhydro sugars from unprotected glycopyranoses by using 2-chloro-1,3-dimethylimidazolinium chloride

Tomonari Tanaka; Wei Chun Huang; Masato Noguchi; Atsushi Kobayashi; Shin ichiro Shoda

doi:10.1016/j.tetlet.2009.02.171

Direct synthesis of 1,6-anhydro sugars from unprotected glycopyranoses by using 2-chloro-1,3-dimethylimidazolinium chloride

Tomonari Tanaka, Wei Chun Huang, Masato Noguchi, Atsushi Kobayashi, Shin ichiro Shoda

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

70 Citations (Scopus)

Abstract

Various 1,6-anhydro sugars have been synthesized directly from the corresponding unprotected glycopyranoses in excellent yields by using 2-chloro-1,3-dimethylimidazolinium chloride (DMC) as a dehydrative condensing agent. The reactions took place smoothly under mild reaction conditions in aqueous media. The present method would be a practical tool for synthesis of 1,6-anhydro derivatives of monosaccharides, linear-oligosaccharides, and branched-oligosaccharides.

Original language	English
Pages (from-to)	2154-2157
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	18
DOIs	https://doi.org/10.1016/j.tetlet.2009.02.171
Publication status	Published - 2009 May 6
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2009.02.171

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title = "Direct synthesis of 1,6-anhydro sugars from unprotected glycopyranoses by using 2-chloro-1,3-dimethylimidazolinium chloride",

abstract = "Various 1,6-anhydro sugars have been synthesized directly from the corresponding unprotected glycopyranoses in excellent yields by using 2-chloro-1,3-dimethylimidazolinium chloride (DMC) as a dehydrative condensing agent. The reactions took place smoothly under mild reaction conditions in aqueous media. The present method would be a practical tool for synthesis of 1,6-anhydro derivatives of monosaccharides, linear-oligosaccharides, and branched-oligosaccharides.",

author = "Tomonari Tanaka and Huang, {Wei Chun} and Masato Noguchi and Atsushi Kobayashi and Shoda, {Shin ichiro}",

note = "Funding Information: This work was supported by a Grant-in Aid for Scientific Research from the Ministry of Education, Sports, Science and Technology, Industrial Technology Research Grant Program in 2006 from NEDO of Japan, and an International Center of Research & Education for Molecular Complex Chemistry in 2007 from TOHOKU UNIVERSITY Global COE Program. ",

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T1 - Direct synthesis of 1,6-anhydro sugars from unprotected glycopyranoses by using 2-chloro-1,3-dimethylimidazolinium chloride

AU - Tanaka, Tomonari

AU - Huang, Wei Chun

AU - Noguchi, Masato

AU - Kobayashi, Atsushi

AU - Shoda, Shin ichiro

N1 - Funding Information: This work was supported by a Grant-in Aid for Scientific Research from the Ministry of Education, Sports, Science and Technology, Industrial Technology Research Grant Program in 2006 from NEDO of Japan, and an International Center of Research & Education for Molecular Complex Chemistry in 2007 from TOHOKU UNIVERSITY Global COE Program.

PY - 2009/5/6

Y1 - 2009/5/6

N2 - Various 1,6-anhydro sugars have been synthesized directly from the corresponding unprotected glycopyranoses in excellent yields by using 2-chloro-1,3-dimethylimidazolinium chloride (DMC) as a dehydrative condensing agent. The reactions took place smoothly under mild reaction conditions in aqueous media. The present method would be a practical tool for synthesis of 1,6-anhydro derivatives of monosaccharides, linear-oligosaccharides, and branched-oligosaccharides.

AB - Various 1,6-anhydro sugars have been synthesized directly from the corresponding unprotected glycopyranoses in excellent yields by using 2-chloro-1,3-dimethylimidazolinium chloride (DMC) as a dehydrative condensing agent. The reactions took place smoothly under mild reaction conditions in aqueous media. The present method would be a practical tool for synthesis of 1,6-anhydro derivatives of monosaccharides, linear-oligosaccharides, and branched-oligosaccharides.

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Direct synthesis of 1,6-anhydro sugars from unprotected glycopyranoses by using 2-chloro-1,3-dimethylimidazolinium chloride

Abstract

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