Stereoselective synthesis of (5′S)-5′-C-(5-bromo-2-penten-1-yl)-2′-deoxyribofuranosyl thymine, a new convertible nucleoside

European Journal of Organic Chemistry

Volumn , Issue 24, 2001, Pages 4693-4700

  Banuls, Valérie ^a   Escudier, Jean Marc ^a   Zedde, Chantal ^a   Claparols, Catherine ^b   Donnadieu, Bruno ^c   Plaisancié, Henri ^b  

^a UPS)   (France)

^b UNIVERSITÉ DE TOULOUSE   (France)

^c LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

Author keywords

Conjugation; Nucleosides; Oligonucleotides; Stereoselectivity

Indexed keywords

5' C (5 BROMO 2 PENTEN 1 YL) 2' DEOXYRIBOFURANOSYLTHYMINE PHOSPHORAMIDITE; DIAMINE; NUCLEOSIDE DERIVATIVE; OLIGODEOXYNUCLEOTIDE; THYMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG CONJUGATION; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR MODEL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; X RAY DIFFRACTION;

EID: 0035661175     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200112)2001:24<4693::AID-EJOC4693>3.0.CO;2-J     Document Type: Article

References (17)

1. E. Uhlmann, A. Peyman, Chem. Rev. 1990, 90, 543-583.
2. A. De Mesmaeker, R. Häner, P. Martin, H. Moser, Acc. Chem. Res. 1995, 28, 366-374.
3. S. T. Crooke, B. Lebleu, Antisense Research and Applications. CRC Press, Boca Raton, FL, 1993.
4. M. Manoharan, T. P. Prakash, I. Barber-Peoc'h, B. Bhat, G. Vasquez, B. S. Ross, P. D. Cook, J. Org. Chent. 1999, 64, 6468-6472.
5. T. H. Smith, M. A. Kent, S. Muthini, S. J. Boone, P. S. Nelson, Nucleosides, Nucleotides. 1996, 15, 1581-1586.
6. C. R. Allerson, S. L. Chen, G. L. Verdine, J. Am. Chemt. Soc. 1997, 119, 7423-7433.
7. J-M. Escudier, I. Tworkowski, L. Bouziani, L. Gorrichon, Tetrahedron Lett. 1996, 37, 4689-4692.
8. V. Banuls, V. Sarramegna, C. Froment, J-M. Escudier, Nucleosides, Nucleotides. 1999, 18, 1527-1529.
9. J. Hovinen, H. Salo, J. Chem. Soc., Perkin. Trans. 1 1997, 3017-3020.
10. V. Banuls, J-M. Escudier, Tetrahedron. 1999, 55, 5831-5838.
11. D. J. Wood, K. K. Ogilvie, F. E. Hruska, Can. J. Chem. 1975, 53, 2781-2790.
12. C. G. Masse, J. S. Panek, Chem. Rev. 1995, 95, 1293-1316.
13. X. Wu, S. Pitsch, Nucleic Acids Res. 1998, 26, 4315-4323.
14. G. Wang, P. J. Middleton, Tetrahedron Lett. 1996, 37, 2739-2742.
15. A. K. Saha, T. J. Caufield, C. Hobbs, D. A. Upson, C. Waychunas, A. M. Yawman, J. Org. Chem. 1995, 60, 788-789.
16. J. Fensholdt, J. Wengel, Acta Chemica Scandinavica 1996, 50, 1157-1163.
17. G. F. Joyce, Proc. Natl. Acad. Sci. USA. 1998, 95, 5845-5847.