223409-46-9Relevant academic research and scientific papers
Synthesis of acyclic carba-nucleoside phosphonates, structural analogues to natural deoxyribonucleotides
Esposito, Annamaria,Perino, Maria Grazia,Taddei, Maurizio
, p. 931 - 936 (2007/10/03)
Acyclic carba-nucleoside phosphonates, modelled on natural deoxyribonucleotides have been prepared starting from DNA nucleobases and tert-butyl acrylate. The products obtained from a Michael-type reaction were elongated to β-oxo esters that were first reduced to β-hydroxy esters and then transformed into protected β-hydroxy aldehydes. Wittig-Homer-Emmons reaction with the anion of tetraisopropyl methylenebisphosphonate gave, after deprotection, the desired 4-hydroxy-6-purinyl- or -6-pyrimidinyl-1- hexenylphosphonic acids. A dimer, potential precursor of acyctic polynucleotides (APN), homomorphous with DNA, was also prepared.
