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Synthesis of Acyclic Carba‐Nucleoside Phosphonates, Structural Analogues to Natural Deoxyribonucleotides
Author(s) -
Esposito Annamaria,
Perino Maria Grazia,
Taddei Maurizio
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199904)1999:4<931::aid-ejoc931>3.0.co;2-r
Subject(s) - chemistry , nucleobase , deoxyribonucleotides , dimer , nucleoside , wittig reaction , deoxyribonucleotide , stereochemistry , dna , polynucleotide , acrylate , nucleoside analogue , nucleotide , organic chemistry , biochemistry , oligonucleotide , monomer , gene , polymer
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.