Aryl H-Phosphonates. 14. Synthesis of New Nucleotide Analogues with Phosphonate−Phosphate Internucleosidic Linkage

<UFIGR ID="ol035166un00001">Aryl nucleoside H-phosphonates <BO>3</BO> and aryl nucleoside P-acylphosphonates <BO>4</BO>, generated in situ from the appropriate H-phosphonate <BO>1</BO> and acylphosphonate monoesters <BO>2</BO>, respectively, reacted rapidly in the presence of tertiary amines to produce in high yields the extended, pyrophosphate analogues, diaryl dinucleoside phosphonate−phosphate derivatives <BO>6</BO>. These, depending on a substituent on the α-carbon of the phosphonate moiety, either underwent transformation into the dinucleoside phosphonate−phosphate <BO>7</BO> or afforded nucleoside H-phosphonates <BO>8</BO> and aryl nucleoside phosphate <BO>9</BO>.