Stereoselective synthesis of β-glycosyl esters of cis-cinnamic acid and its derivatives using unprotected glycosyl donors

Kazumasa Matsuo; Keisuke Nishikawa; Mitsuru Shindo

doi:10.1016/j.tetlet.2011.08.104

Stereoselective synthesis of β-glycosyl esters of cis-cinnamic acid and its derivatives using unprotected glycosyl donors

Kazumasa Matsuo, Keisuke Nishikawa, Mitsuru Shindo

Department of Fundamental Organic Chemistry

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

13 Citations (Scopus)

Abstract

The β-glycosyl esters of cis-cinnamic acid were synthesized directly using Hannesian's unprotected glycosyl donor and the carboxylic acid in toluene. This protocol does not require protecting groups on the glycosyl donors, and high stereoselectivity was achieved. The first synthesis of a potent allelochemical, 1-O-cis-cinnamoyl-β-d-glucopyranose, is also described.

Original language	English
Pages (from-to)	5688-5692
Number of pages	5
Journal	Tetrahedron Letters
Volume	52
Issue number	43
DOIs	https://doi.org/10.1016/j.tetlet.2011.08.104
Publication status	Published - Oct 26 2011

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2011.08.104

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title = "Stereoselective synthesis of β-glycosyl esters of cis-cinnamic acid and its derivatives using unprotected glycosyl donors",

abstract = "The β-glycosyl esters of cis-cinnamic acid were synthesized directly using Hannesian's unprotected glycosyl donor and the carboxylic acid in toluene. This protocol does not require protecting groups on the glycosyl donors, and high stereoselectivity was achieved. The first synthesis of a potent allelochemical, 1-O-cis-cinnamoyl-β-d-glucopyranose, is also described.",

author = "Kazumasa Matsuo and Keisuke Nishikawa and Mitsuru Shindo",

note = "Funding Information: This research was partially supported by a Grant-in-Aid for Scientific Research on (B) (22390002) and the Program for Promotion of Basic and Applied Research for Innovations in the Bio-oriented Industry (BRAIN). K.M. additionally acknowledges the support of the JSPS. ",

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AU - Matsuo, Kazumasa

AU - Nishikawa, Keisuke

AU - Shindo, Mitsuru

N1 - Funding Information: This research was partially supported by a Grant-in-Aid for Scientific Research on (B) (22390002) and the Program for Promotion of Basic and Applied Research for Innovations in the Bio-oriented Industry (BRAIN). K.M. additionally acknowledges the support of the JSPS.

PY - 2011/10/26

Y1 - 2011/10/26

N2 - The β-glycosyl esters of cis-cinnamic acid were synthesized directly using Hannesian's unprotected glycosyl donor and the carboxylic acid in toluene. This protocol does not require protecting groups on the glycosyl donors, and high stereoselectivity was achieved. The first synthesis of a potent allelochemical, 1-O-cis-cinnamoyl-β-d-glucopyranose, is also described.

AB - The β-glycosyl esters of cis-cinnamic acid were synthesized directly using Hannesian's unprotected glycosyl donor and the carboxylic acid in toluene. This protocol does not require protecting groups on the glycosyl donors, and high stereoselectivity was achieved. The first synthesis of a potent allelochemical, 1-O-cis-cinnamoyl-β-d-glucopyranose, is also described.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Stereoselective synthesis of β-glycosyl esters of cis-cinnamic acid and its derivatives using unprotected glycosyl donors

Abstract

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