Commercially available 5′-DMT phosphoramidites as reagents for the synthesis of Vinylphosphonate-linked Oligonucleic acids

Organic Letters

Volumn 3, Issue 21, 2001, Pages 3365-3367

  Abbas, Sahar ^a   Bertram, Richard D ^a   Hayes, Christopher J ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; OLIGONUCLEOTIDE; ORGANOPHOSPHORUS COMPOUND; PHOSPHONIC ACID DERIVATIVE; PHOSPHORAMIDIC ACID; PHOSPHORIC ACID; VINYL DERIVATIVE; VINYLPHOSPHONIC ACID;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

AMIDES; MOLECULAR STRUCTURE; OLIGONUCLEOTIDES; ORGANOPHOSPHORUS COMPOUNDS; PHOSPHONIC ACIDS; PHOSPHORIC ACIDS; VINYL COMPOUNDS;

EID: 0035909629     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0166045     Document Type: Article

References (17)

1. (a) Uhlmann, E.; Peyman, A. Chem. Rev. 1990, 90, 543.
2. (b) Szymkowski, D. E. Drug Discovery Today 1996, 1, 415.
3. (c) Englisch, U.; Gauss, D. H. Angew. Chem., Int. Ed. Engl. 1991, 30, 613.
4. (d) Uhlmann, E.; Peyman, A.; Breipohl, G.; Will, D. W. Angew. Chem., Int. Ed. 1998, 37, 2191.
5. (a) Abbas, S.; Hayes, C. J. Tetrahedron Lett. 2000, 41, 4513.
6. (b) Abbas, S.; Hayes, C. J., Synlett 1999, 1124.
7. For an alternative route to vinylphosphonate-linked nucleic acids, see also: (c) Zhao, Z.; Caruthers, M. H. Tetrahedron Lett. 1996, 37, 6239.
8. Lei, H.; Stoakes, M. S.; Schwabacher, A. W. Synthesis 1992, 1255.
9. 2 gel column chromatography lead to substantial decomposition of the H-phosphonates and provided only poor yields of the desired coupling partners.
10. The asterisk (*) signifies the position of the vinylphosphonate internucleotide linkage.
11. McBride, L. J.; Caruthers, M. H. Tetrahedron Lett. 1983, 24, 245.
12. Bannwarth, W.; Trzeciak, A. Helv. Chim. Acta 1987, 70, 175.
13. 31P NMR.
14. Caruthers, M. H. Science 1985, 230, 281.
15. Caruthers and Zhao have also reported the solid-phase synthesis of vinylphosphonate linked oligonucleic acids (see ref 2c). In their case, however, they used an o-chlorophenyl group for protection of the phosphonate internucleotide linkage and an extra synthetic step was needed for its deprotection.
16. The only other product to be isolated from the automated synthesis was thymidine, which results from the incomplete coupling of the phosphoramidite 20 to the 5′-OH of the initial CPG-supported thymidine (corresponding to T4 in 22 (Figure 2)).
17. For copies of relevant spectra see Supporting Information.