Aryl h-phosphonates. 14. Synthesis of new nucleotide analogues with phosphonate-phosphate internucleosidic linkage.
[reaction: see text] Aryl nucleoside H-phosphonates 3 and aryl nucleoside P-acylphosphonates 4, generated in situ from the appropriate H-phosphonate 1 and acylphosphonate monoesters 2, respectively, reacted rapidly in the presence of tertiary amines to produce in high yields the extended, pyrophosphate analogues, diaryl dinucleoside phosphonate-phosphate derivatives 6. These, depending on a substituent on the alpha-carbon of the phosphonate moiety, either underwent transformation into the dinucleoside phosphonate-phosphate 7 or afforded nucleoside H-phosphonates 8 and aryl nucleoside phosphate 9.
D009705:Nucleosides / Q000737:chemistry*; D009711:Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D010755:Organophosphates / Q000737:chemistry*; D063065:Organophosphonates / Q000737:chemistry*
D009705:Nucleosides; D009711:Nucleotides; D010755:Organophosphates; D063065:Organophosphonates