Issue 21, 2017

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

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.

Graphical abstract: 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

Supplementary files

Article information

Article type
Communication
Submitted
12 Jan 2017
Accepted
20 Feb 2017
First published
20 Feb 2017

Chem. Commun., 2017,53, 3018-3021

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

N. Nishi, J. Nashida, E. Kaji, D. Takahashi and K. Toshima, Chem. Commun., 2017, 53, 3018 DOI: 10.1039/C7CC00269F

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