Synthesis of enantiomerically pure D-FDOC, an anti-HIV agent.
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.
Mao
Shuli
S
Department of Chemistry, Emory University, 403 Cherry Logan Emerson Hall, 1521 Dickey Drive, Atlanta, GA 30322, USA.
Bouygues
Martin
M
Welch
Christopher
C
Biba
Mirlinda
M
Chilenski
Jen
J
Schinazi
Raymond F
RF
Liotta
Dennis C
DC
D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D003562:Cytidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D013237:Stereoisomerism
C498026:2',3'-dideoxy-5-fluoro-oxacytidine; D019380:Anti-HIV Agents; D003562:Cytidine