Synthesis of meso-2′,3′-dideoxy-3′β-hydroxymethyl carbocyclic nucleosides as potential antiviral drugs. Unusual competitive 2-O-versus N1-alkylation of 3-substituted pyrimidines under Mitsunobu conditions

Abstract

The synthesis of meso-2′,3′-dideoxy-3′β-hydroxymethyl carbocyclic nucleosides as potential antiviral drugs via the alkylation of protected purines and pyrimidines with meso-β,β′-disubstituted cyclopentanols under Mitsunobu conditions is described. Chemical evidence for an unusual competitive 2-O-vs. N¹-alkylation of 3-substituted pyrimidines is presented.