title: Regioselective and 1,2-cis-α-Stereoselective Glycosylation Utilizing Glycosyl-Acceptor-Derived Boronic Ester Catalyst.
abstract: Regioselective and 1,2-cis-α-stereoselective glycosylations using 1α,2α-anhydro glycosyl donors and diol glycosyl acceptors in the presence of a glycosyl-acceptor-derived boronic ester catalyst. The reactions proceed smoothly to give the corresponding 1,2-cis-α-glycosides with high stereo- and regioselectivities in high yields without any further additives under mild reaction conditions. In addition, the present glycosylation method was successfully applied to the synthesis of an isoflavone glycoside.
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522 (Japan).
authors.forename: Akira
authors.initials: A
authors.lastname: Nakagawa
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522 (Japan).
authors.forename: Masamichi
authors.initials: M
authors.lastname: Tanaka
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522 (Japan).
authors.forename: Shun
authors.initials: S
authors.lastname: Hanamura
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.
authors.forename: Daisuke
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). toshima@applc.keio.ac.jp.
authors.forename: Kazunobu
authors.initials: K
authors.lastname: Toshima
mesh_terms: D001895:Boron / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D006031:Glycosylation; D013237:Stereoisomerism
chemical_list: D004952:Esters; D001895:Boron
keywords: boron; glycosylation; regioselectivity; stereoselectivity; synthetic methods