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Updated: Feb 15, 2026

Nucleoside Triphosphates - From Synthesis to Biochemical Characterization
Published on: April 3, 2014
Synthesis of a C-Nucleoside Phosphonate by Base-Promoted Epimerization
Peng Nie1, Elisabetta Groaz1, Steven De Jonghe2
1Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven , Herestraat 49, 3000 Leuven, Belgium.
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.
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