William B. Marvin

Diastereoselective Synthesis of 2′-Deoxy and 2′-O-Methyl Dinucleoside (3′ 5′)-Methylphosphonates via Alkoxymagnesium Chloride-Mediated Nucleoside Coupling

Abstract A diastereoselective dinucleoside methylphosphonate synthetic method that features coupling of diastereomerically pure 1,1,1,3,3,3-hexafluoro-2-propyl nucleoside-3′-O-methylphosphonate monomers with 3′-O-protected nucleoside monomers mediated by alkoxymagnesium chloride reagents is described. This synthetic method was found to be diastereospecific in the synthesis of selected 2′-deoxy dinucleoside methyphosphonates and diastereoselective in the synthesis of all sixteen 2′-O-methyl dinucleoside methylphosphonates.