title: Diastereoselective Synthesis of C2'-Fluorinated Nucleoside Analogues Using an Acyclic Approach.
abstract: Nucleoside analogues bearing a fluorine in the C2'-position have been synthesized by SN2-like cyclizations of acyclic thioaminal precursors. This strategy provides access to two scaffolds, d-1',2'-cis-thiofuranosides and d-1',2'-trans-furanosides, which are difficult to generate using the standard approach for nucleoside synthesis. The addition of silylated nucleobases onto model C2-fluorinated dithioacetal substrates resulted in 1,2-syn diastereoselectivity, which is consistent with the C2-F and S-alkyl moiety being in close proximity. A new series of analogues bearing a C3' all-carbon quaternary center along with a C2'-F atom have also been synthesized using this approach and are being investigated as potential antimetabolites.
authors.affiliation: Bio-organic Chemistry Laboratory, Institut de Recherches Cliniques de Montréal (IRCM) , Montréal, Québec H2W 1R7, Canada.|Department of Chemistry, McGill University , Montréal, Québec H3A 2K6, Canada.
authors.forename: Starr
authors.initials: S
authors.lastname: Dostie
authors.affiliation: Bio-organic Chemistry Laboratory, Institut de Recherches Cliniques de Montréal (IRCM) , Montréal, Québec H2W 1R7, Canada.
authors.forename: Michel
authors.initials: M
authors.lastname: Prévost
authors.affiliation: Bio-organic Chemistry Laboratory, Institut de Recherches Cliniques de Montréal (IRCM) , Montréal, Québec H2W 1R7, Canada.
authors.forename: Philippe
authors.initials: P
authors.lastname: Mochirian
authors.affiliation: Bio-organic Chemistry Laboratory, Institut de Recherches Cliniques de Montréal (IRCM) , Montréal, Québec H2W 1R7, Canada.
authors.forename: Kashif
authors.initials: K
authors.lastname: Tanveer
authors.affiliation: Bio-organic Chemistry Laboratory, Institut de Recherches Cliniques de Montréal (IRCM) , Montréal, Québec H2W 1R7, Canada.
authors.forename: Nicholas
authors.initials: N
authors.lastname: Andrella
authors.affiliation: Bio-organic Chemistry Laboratory, Institut de Recherches Cliniques de Montréal (IRCM) , Montréal, Québec H2W 1R7, Canada.
authors.forename: Ariana
authors.initials: A
authors.lastname: Rostami
authors.affiliation: Bio-organic Chemistry Laboratory, Institut de Recherches Cliniques de Montréal (IRCM) , Montréal, Québec H2W 1R7, Canada.|Department of Chemistry, Université de Montréal , Montréal, Québec H3C 3J7, Canada.
authors.forename: Guillaume
authors.initials: G
authors.lastname: Tambutet
authors.affiliation: Bio-organic Chemistry Laboratory, Institut de Recherches Cliniques de Montréal (IRCM) , Montréal, Québec H2W 1R7, Canada.|Department of Chemistry, Université de Montréal , Montréal, Québec H3C 3J7, Canada.|Department of Chemistry, McGill University , Montréal, Québec H3A 2K6, Canada.
authors.forename: Yvan
authors.initials: Y
authors.lastname: Guindon