title: Dual-face nucleoside scaffold featuring a stereogenic all-carbon quaternary center. Intramolecular silicon tethered group-transfer reaction.
abstract: The design of a novel nucleoside scaffold that exhibits an all-carbon quaternary center is reported. This allows for both α- and β-anomers of a given 2'-deoxy-2',2'-difluoro nucleoside analog (NA) to have potential biological activity. Using an intramolecular atom-transfer reaction, an all-carbon quaternary center was obtained without the use of heavy metals and/or harsh conditions. The chemistry developed is efficient, easily scalable and leads to novel libraries of molecules.
authors.affiliation: Bio-Organic Chemistry Laboratory, Institut de Recherches Cliniques de Montréal (IRCM) , Montréal, Québec H2W 1R7, Canada.
authors.forename: Guillaume
authors.initials: G
authors.lastname: Tambutet
authors.forename: Fabiola
authors.initials: F
authors.lastname: Becerril-Jiménez
authors.forename: Starr
authors.initials: S
authors.lastname: Dostie
authors.forename: Ryan
authors.initials: R
authors.lastname: Simard
authors.forename: Michel
authors.initials: M
authors.lastname: Prévost
authors.forename: Philippe
authors.initials: P
authors.lastname: Mochirian
authors.forename: Yvan
authors.initials: Y
authors.lastname: Guindon
mesh_terms: D002384:Catalysis; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry*; D012825:Silicon / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D009705:Nucleosides; D012825:Silicon