对映体纯的抗艾滋病毒药物D-FDOC的合成。

Synthesis of enantiomerically pure D-FDOC, an anti-HIV agent.

作者信息

Mao Shuli, Bouygues Martin, Welch Christopher, Biba Mirlinda, Chilenski Jen, Schinazi Raymond F, Liotta Dennis C

机构信息

Department of Chemistry, Emory University, 403 Cherry Logan Emerson Hall, 1521 Dickey Drive, Atlanta, GA 30322, USA.

出版信息

Bioorg Med Chem Lett. 2004 Oct 4;14(19):4991-4. doi: 10.1016/j.bmcl.2004.07.016.

DOI:10.1016/j.bmcl.2004.07.016

PMID:15341966

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.

摘要

FDOC（2'，3'-二脱氧-5-氟氧杂胞苷）的β-D-对映体具有强大的抗HIV-1活性。通过采用串联动力学拆分/手性盐结晶方案，以光学纯形式获得了该对映体。此外，还开发了一些条件，使FDOC的L-对映体中不需要的丁酸酯能够外消旋化。然后，这种物质可以在未来的拆分中循环利用。