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Digitale Medien

Synthesis of Acyclic Carba-Nucleoside Phosphonates, Structural Analogues to Natural Deoxyribonucleotides (1999)

Esposito, Annamaria ; Perino, Maria Grazia ; Taddei, Maurizio

Weinheim : Wiley-Blackwell

Liebigs Annalen 1999 (1999), S. 931-936

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Details

ISSN: 1434-193X

Schlagwort(e): Nucleosides ; Phosphonates ; Nucleophilic additions ; C-C coupling ; Reduction ; Chemistry ; General Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: -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.

Materialart: Digitale Medien

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