title: Electrooxidative glycosylation through C-S bond cleavage of 1-arylthio-2,3-dideoxyglycosides. Synthesis of 2',3'-dideoxynucleosides.
abstract: [reaction: see text] The electrooxidative glycosylation of newly designed 1-arylthio-substituted 2,3-dideoxyglycosides is described. The halide salt-mediated electrooxidation utilizing either of the alpha- or beta-thiodideoxyglycosides proceeded smoothly at -78 degrees C to give dideoxynucleosides in a beta-selective manner, presumably through a 1-halo-substituted glycosyl donor.
authors.affiliation: Department of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-Naka, Okayama 700-8530, Japan.
authors.forename: Koichi
authors.initials: K
authors.lastname: Mitsudo
authors.forename: Takashi
authors.initials: T
authors.lastname: Kawaguchi
authors.forename: Seiji
authors.initials: S
authors.lastname: Miyahara
authors.forename: Wataru
authors.initials: W
authors.lastname: Matsuda
authors.forename: Manabu
authors.initials: M
authors.lastname: Kuroboshi
authors.forename: Hideo
authors.initials: H
authors.lastname: Tanaka
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry; D015224:Dideoxynucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D004563:Electrochemistry; D006031:Glycosylation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013865:Thioglycosides / Q000737:chemistry*
chemical_list: D019380:Anti-HIV Agents; D015224:Dideoxynucleosides; D013865:Thioglycosides