ISSN:
1434-193X
Keywords:
Nucleosides
;
Phosphonates
;
Nucleophilic additions
;
C-C coupling
;
Reduction
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
-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-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.
Type of Medium:
Electronic Resource
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