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.

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.