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

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22 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 languageEnglish
Pages (from-to)3018-3021
Number of pages4
JournalChemical Communications
Volume53
Issue number21
DOIs
Publication statusPublished - 2017

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Mannosides
Boronic Acids
Glycosylation
Stereoselectivity
Sugars
Escherichia coli
Lipopolysaccharides
Catalysts
Acids

ASJC Scopus subject areas

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

Cite this

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T1 - 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

AU - Nishi, Nobuya

AU - Nashida, Junki

AU - Kaji, Eisuke

AU - Takahashi, Daisuke

AU - Toshima, Kazunobu

PY - 2017

Y1 - 2017

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AB - 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.

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