Commercially available 5'-DMT phosphoramidites as reagents for the synthesis of vinylphosphonate-linked oligonucleic acids.
[reaction: see text]. Commercially available cyanoethyl phosphoramidites derived from T, d(C), d(A), and d(G) were hydrolyzed (1H-tetrazole, MeCN/H2O) to give the corresponding H-phosphonates in excellent yields. Palladium(0)-catalyzed cross-coupling of each of these with the thymidine-derived vinylbromide 2 afforded the corresponding vinylphosphonate-linked dimers TT, d(C)T, d(A)T, and d(G)T in modest to good yields. The TT dimer was further elaborated to give a 5'-DMT-TT-3'-CEP building block, and this was used in the automated synthesis of the TpTTpT tetramer.
Abbas
S
S
The School of Chemistry, The University of Nottingham, University Park, Nottingham NG7 2RD, UK.
Bertram
R D
RD
Hayes
C J
CJ
D000577:Amides / Q000737:chemistry; D015394:Molecular Structure; D009841:Oligonucleotides / Q000138:chemical synthesis*; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry; D010756:Phosphoric Acids / Q000737:chemistry; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000577:Amides; D009841:Oligonucleotides; D063065:Organophosphonates; D009943:Organophosphorus Compounds; D010756:Phosphoric Acids; D014753:Vinyl Compounds; C433467:vinylphosphonic acid; C011067:phosphoramidic acid