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.
Synthesis of a C-Nucleoside Phosphonate by Base-Promoted Epimerization
Groaz E.;
2018
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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