title: Glycosyl sulfonium ions as storable intermediates for glycosylations.
abstract: Glycosyl sulfonium ions, which serve as persistent glycosyl cation equivalents, were prepared by the addition of diorganosulfides to an electrochemically generated glycosyl triflate. Low-temperature and variable-temperature NMR studies were performed to reveal the structure, stability, and reactivity of glycosyl sulfonium ions. The glycosyl sulfonium ions could be used as storable intermediates for reactions with various glycosyl acceptors including thioglycosides to give the corresponding disaccharides.
authors.affiliation: Department of Synthetic Chemistry, Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan.
authors.forename: Toshiki
authors.initials: T
authors.lastname: Nokami
authors.forename: Yuki
authors.initials: Y
authors.lastname: Nozaki
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Saigusa
authors.forename: Akito
authors.initials: A
authors.lastname: Shibuya
authors.forename: Shino
authors.initials: S
authors.lastname: Manabe
authors.forename: Yukishige
authors.initials: Y
authors.lastname: Ito
authors.forename: Jun-ichi
authors.initials: J
authors.lastname: Yoshida
mesh_terms: D020650:Combinatorial Chemistry Techniques; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D006031:Glycosylation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013452:Sulfonium Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D006027:Glycosides; D013452:Sulfonium Compounds