Regio- and stereoselective β-mannosylation using a boronic acid catalyst and its application in the synthesis of a tetrasaccharide repeating unit of lipopolysaccharide derived from E. coli O75

Nobuya Nishi; Junki Nashida; Eisuke Kaji; Daisuke Takahashi; Kazunobu Toshima

doi:10.1039/c7cc00269f

Regio- and stereoselective β-mannosylation using a boronic acid catalyst and its application in the synthesis of a tetrasaccharide repeating unit of lipopolysaccharide derived from E. coli O75

Nobuya Nishi, Junki Nashida, Eisuke Kaji, Daisuke Takahashi, Kazunobu Toshima

Department of Applied Chemistry

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

54 Citations (Scopus)

Abstract

Regio- and stereoselective β-mannosylations using 1,2-anhydromannose and diol sugar acceptors in the presence of a boronic acid catalyst proceeded smoothly to give the corresponding β-mannosides with high regio- and β-stereoselectivities in high yields without further additives under mild conditions. In addition, this glycosylation method was applied successfully to the synthesis of a tetrasaccharide repeating unit of lipopolysaccharide (LPS) derived from E. coli O75.

Original language	English
Pages (from-to)	3018-3021
Number of pages	4
Journal	Chemical Communications
Volume	53
Issue number	21
DOIs	https://doi.org/10.1039/c7cc00269f
Publication status	Published - 2017

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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Regio- and stereoselective β-mannosylation using a boronic acid catalyst and its application in the synthesis of a tetrasaccharide repeating unit of lipopolysaccharide derived from E. coli O75. / Nishi, Nobuya; Nashida, Junki; Kaji, Eisuke et al.
In: Chemical Communications, Vol. 53, No. 21, 2017, p. 3018-3021.

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

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AU - Kaji, Eisuke

AU - Takahashi, Daisuke

AU - Toshima, Kazunobu

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Regio- and stereoselective β-mannosylation using a boronic acid catalyst and its application in the synthesis of a tetrasaccharide repeating unit of lipopolysaccharide derived from E. coli O75

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