Synthesis of a C-Nucleoside Phosphonate by Base-Promoted Epimerization

Org Lett. 2018 Feb 16;20(4):1203-1206. doi: 10.1021/acs.orglett.8b00123. Epub 2018 Feb 1.

Abstract

The efficient synthesis of a [2'S] C-nucleoside phosphonate and its corresponding prodrug has been realized. A phosphonomethoxy group was stereoselectively introduced at the anomeric 5'-carbon atom through glycosylation of a benzoyl protected [5'R]-acetoxy-[2'R]-9-deazaadenine. An unexpected epimerization at the 2'-position of the sugar moiety occurred upon removal of the protecting groups, but this was further exploited as a key reaction for improved synthesis of the target compound.

Publication types

  • Research Support, Non-U.S. Gov't