title: 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.
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan. dtak@applc.keio.ac.jp toshima@applc.keio.ac.jp.
authors.forename: Nobuya
authors.initials: N
authors.lastname: Nishi
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan. dtak@applc.keio.ac.jp toshima@applc.keio.ac.jp.
authors.forename: Junki
authors.initials: J
authors.lastname: Nashida
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan. dtak@applc.keio.ac.jp toshima@applc.keio.ac.jp.
authors.forename: Eisuke
authors.initials: E
authors.lastname: Kaji
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan. dtak@applc.keio.ac.jp toshima@applc.keio.ac.jp.
authors.forename: Daisuke
authors.identifier: http://orcid.org/0000-0003-3222-6648
authors.initials: D
authors.lastname: Takahashi
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan. dtak@applc.keio.ac.jp toshima@applc.keio.ac.jp.
authors.forename: Kazunobu
authors.identifier: http://orcid.org/0000-0003-3994-9099
authors.initials: K
authors.lastname: Toshima
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D004926:Escherichia coli / Q000737:chemistry*; D008070:Lipopolysaccharides / Q000737:chemistry*; D008362:Mannosides / Q000138:chemical synthesis* / Q000737:chemistry; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001897:Boronic Acids; D008070:Lipopolysaccharides; D008362:Mannosides; D009844:Oligosaccharides