title: Synthesis of enantiomerically pure D-FDOC, an anti-HIV agent.
abstract: The beta-D-enantiomer of FDOC (2',3'-dideoxy-5-fluoro-oxacytidine) exhibits potent anti-HIV-1 activity. It was obtained in optically pure form by employing a tandem kinetic resolution/chiral salt crystallization protocol. In addition, conditions were developed that allowed the unwanted butyrate ester of the L-enantiomer of FDOC to be racemized. This material could then be recycled in future resolutions.
authors.affiliation: Department of Chemistry, Emory University, 403 Cherry Logan Emerson Hall, 1521 Dickey Drive, Atlanta, GA 30322, USA.
authors.forename: Shuli
authors.initials: S
authors.lastname: Mao
authors.forename: Martin
authors.initials: M
authors.lastname: Bouygues
authors.forename: Christopher
authors.initials: C
authors.lastname: Welch
authors.forename: Mirlinda
authors.initials: M
authors.lastname: Biba
authors.forename: Jen
authors.initials: J
authors.lastname: Chilenski
authors.forename: Raymond F
authors.initials: RF
authors.lastname: Schinazi
authors.forename: Dennis C
authors.initials: DC
authors.lastname: Liotta
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D003562:Cytidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: C498026:2',3'-dideoxy-5-fluoro-oxacytidine; D019380:Anti-HIV Agents; D003562:Cytidine