Synthesis of nucleic acid fragments with 3′-deoxy-3′-C-methylenephosphonate linkages - Oxidation of nucleoside 3′-deoxy-3′-C-methylenephosphinate esters

European Journal of Organic Chemistry

Volumn , Issue 18, 2002, Pages 3140-3144

  Winqvist, Anna ^a   Strömberg, Roger ^a  

^a KAROLINSKA INSTITUTE   (Sweden)

Author keywords

Catalysis; Iodine; Oligonucleotides; Oxidation

Indexed keywords

NUCLEIC ACID; NUCLEOSIDE DERIVATIVE; PHOSPHINE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; PYRIDINE DERIVATIVE; PYRIDINIUM DERIVATIVE; THYMIDINE 5' (URIDINE 3' DEOXY 3' METHYLENEPHOSPHINATE); THYMIDINE 5' (URIDINE 3' DEOXY 3' METHYLENEPHOSPHONATE); TRIETHYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; SYNTHESIS;

EID: 0036738769     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200209)2002:18<3140::AID-EJOC3140>3.0.CO;2-X     Document Type: Article

References (22)

1. S. M. Freier, K-H. Altmann, Nucleic Acids Res. 1997, 25, 4429-4443.
2. M. Warashina, Y. Takagi, W. J. Stec, K. Taira, Curr Opin. Biotechnol. 2000, 11, 354-362.
3. G. H. Jones, H. P. Albrecht, N. P. Damodaran, J. G. Moffatt, J. Am. Chem. Soc. 1970, 92, 5510-5511.
4. A. Mazur, B. E. Tropp, R. Engel, Tetrahedron 1984, 40, 3949-3956.
5. S. P. Collingwood, M. E. Douglas, F. Natt, U. Pieles, Phosporus Sulfur Silicon 1999, 144-146, 645-648.
6. P. D. Cook, M. Manoharan, M. Maier, H. An, PCT Int. Appl., 2001, 110 pp. (WO 01/02419).
7. J. Stawinski, R. Strömberg, T. Szabo, Coll. Czech. Chem. Commun. 1990, 55, 145-148.
8. A. Winqvist, R. Strömberg, Eur. J. Org. Chem. 2001, 4305-4311.
9. A. Winqvist, R. Strömberg, Eur. J. Org. Chem. 2002, 1509-1515.
10. A. Winqvist, R. Strömberg, to be submitted to Eur. J. Org. Chem. supplementary material available from the authors.
11. P. J. Garegg, T. Regberg, J. Stawinski, R. Strömberg, Chem. Scr. 1985, 25, 280-282.
12. P. J. Garegg, T. Regberg, J. Stawinski, R. Strömberg, Chem. Scr. 1986, 26, 59-62.
13. B. C. Froehler, M. D. Matteucci, Tetrahedron Lett. 1986, 27, 469-472.
14. P. J. Garegg, I. Lindh, T. Regberg, J. Stawinski, R. Strömberg, C. Henrichson, Tetrahedron Lett. 1986, 27, 4051-4054.
15. P. J. Garegg, I. Lindh, T. Regberg, J. Stawinski, R. Strömberg, C. Henrichson, Tetrahedron Lett. 1986, 27, 4055-4058.
16. B. C. Froehler, P. G. Ng, M. D. Matteucci, Nucl. Acids Res. 1986, 14, 5399-5407.
17. P. J. Garegg, T. Regberg, J. Stawinski, R. Strömberg, J. Chem. Soc., Perkin Trans. 1 1987, 1269-1273.
18. P. Nylen, Z. Anorg. Allg. Chem. 1938, 235, 161-182.
19. E. S. Lewis, L. G. Spears, J. Am. Chem. Soc. 1985, 107, 3918-3921.
20. P. M. Cullis, M. Lee, J. Chem. Soc., Chem. Commun. 1992, 1207-1208.
21. E. De Vroom, M. L. Spierenburg, C. E. Dreef, G. A. Van der Marel, J. H. Van Boom, Recl. Trav. Chim. Pays-Bas 1987, 65-66.
22. E. N. Tsvetkov, M. I. Terekhova, E. S. Petrov, R. A. Malevannaya, S. P. Mesyats, A. I. Shatenshtein, M. I. Kabachnik, Izv. Akad. Nauk SSSR, Ser. Khim. 1978, 1981-1984.