Synthesis of Acyclic Carba-Nucleoside Phosphonates, Structural Analogues to Natural Deoxyribonucleotides

✍ Scribed by Annamaria Esposito; Maria Grazia Perino; Maurizio Taddei

• Book ID: 101279124
• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 264 KB
• Volume: 1999
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199904)1999:4<931::aid-ejoc931>3.0.co;2-r

✦ Synopsis

Acyclic carba-nucleoside phosphonates, modelled on natural Wittig-Horner-Emmons reaction with the anion of tetraisopropyl methylenebisphosphonate gave, after deoxyribonucleotides have been prepared starting from DNA nucleobases and tert-butyl acrylate. The products deprotection, the desired 4-hydroxy-6-purinyl-or -6pyrimidinyl-1-hexenylphosphonic acids. A dimer, potential obtained from a Michael-type reaction were elongated to βoxo esters that were first reduced to β-hydroxy esters and precursor of acyclic polynucleotides (APN), homomorphous with DNA, was also prepared. then transformed into protected β-hydroxy aldehydes.