An improved procedure for the synthesis of vinylphosphonate-linked nucleic acids

Tetrahedron Letters

Volumn 41, Issue 22, 2000, Pages 4513-4517

  Abbas, Sahar ^a   Hayes, Christopher J ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

Antisense; Modified backbone; Oligonucleotide; Palladium coupling; Vinyl bromide

Indexed keywords

NUCLEOTIDE DERIVATIVE; PALLADIUM; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0034622058     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00653-5     Document Type: Article

References (15)

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4. (a) Of the more recent modifications, the protein nucleic acids (PNAs) are worthy of special note. For a comprehensive review, see: Uhlmann, E.; Peyman, A.; Breipohl, G.; Will, D. W. Angew. Chem., Int. Ed. Engl. 1998, 37, 2797;
5. ™), based upon a phosphorothioate internucleotide linkage, was approved by the FDA in August 1998 for treatment of CMV retinitis (for more details please see the Isis pharmaceuticals web site at www.isip.com).
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14. Lei, H.; Stoakes, M. S.; Schwabacher, A. W. Synthesis 1992, 1255.
15. The H-phosphonate 12 was synthesised in a similar manner to the H-phosphonate 2, which we have reported previously. The synthesis involves selective TBS-5′-protection of commercially available N-benzoyl-2′-deoxyadenosine, coupling with N,N-diisopropylmethylphosphonamidic chloride and then tetrazole-mediated hydrolysis in methylene chloride.