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 beta-oxo esters that were first reduced to beta-hydroxy esters and then transformed into protected beta-hydroxy aldehydes. Wittig-Horner-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 acyclic polynucleotides (APN), homomorphous with DNA, was also prepared.
Esposito, A., Perino, M.G., Taddei, M. (1999). Synthesis of acyclic carba-nucleoside phosphonates, structural analogues to natural deoxyribonucleotides. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1999(4), 931-936 [10.1002/(SICI)1099-0690(199904)1999:4<931::AID-EJOC931>3.0.CO;2-R].
Synthesis of acyclic carba-nucleoside phosphonates, structural analogues to natural deoxyribonucleotides
Taddei, Maurizio
1999-01-01
Abstract
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 beta-oxo esters that were first reduced to beta-hydroxy esters and then transformed into protected beta-hydroxy aldehydes. Wittig-Horner-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 acyclic polynucleotides (APN), homomorphous with DNA, was also prepared.
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https://hdl.handle.net/11365/30384
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