title: Synthesis of N-glycosides. An alternative approach based on diastereoselective base coupling and S(N)2 cyclization.
abstract: [reaction: see text] Acyclic diastereoselection is achieved for the formation of thioaminyl acetals. The highly intramolecular stereocontrolled S(N)2 displacement of the thioaminyls allows for the formation of cyclic nucleoside derivatives. This versatile approach may provide easy access to a large variety of N-glycosides.
authors.affiliation: Institut de recherches cliniques de Montréal (IRCM), Bio-organic Chemistry Laboratory, 110 avenue des Pins Ouest, Montréal, Québec, Canada H2W 1R7. guindoy@ircm.qc.ca
authors.forename: Yvan
authors.initials: Y
authors.lastname: Guindon
authors.forename: Marc
authors.initials: M
authors.lastname: Gagnon
authors.forename: Isabelle
authors.initials: I
authors.lastname: Thumin
authors.forename: Daniel
authors.initials: D
authors.lastname: Chapdelaine
authors.forename: Grace
authors.initials: G
authors.lastname: Jung
authors.forename: Brigitte
authors.initials: B
authors.lastname: Guérin
mesh_terms: D000606:Amino Sugars / Q000138:chemical synthesis; D003500:Cyclization; D006027:Glycosides / Q000138:chemical synthesis*; D009705:Nucleosides / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D000606:Amino Sugars; D006027:Glycosides; D009705:Nucleosides