title: A diastereoselective synthesis of 5'-substituted-uridine derivatives.
abstract: A straightforward strategy for the synthesis of 5'-substituted-uridine derivatives is described. It relies on the introduction of various substituents at C-5' at the last step of the synthesis by regioselective nucleophilic opening of a unique epoxide that provides access to a small library of compounds. This epoxide results from the diastereoselective epoxidation, performed at a multigram scale, of a uridine-derived alkene. The configuration of the newly created 5' asymmetric center has been unambiguously assigned by X-ray diffraction analysis.
authors.affiliation: Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, Université Paris Descartes, UMR 8601 CNRS , 45 rue des Saints Pères, 75006 Paris, France.
authors.forename: Mickaël J
authors.initials: MJ
authors.lastname: Fer
authors.forename: Pierre
authors.initials: P
authors.lastname: Doan
authors.forename: Thierry
authors.initials: T
authors.lastname: Prangé
authors.forename: Sandrine
authors.initials: S
authors.lastname: Calvet-Vitale
authors.forename: Christine
authors.initials: C
authors.lastname: Gravier-Pelletier
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014529:Uridine / Q000031:analogs & derivatives* / Q000737:chemistry*; D014961:X-Ray Diffraction
chemical_list: D000475:Alkenes; D004852:Epoxy Compounds; D014529:Uridine