A mild and highly selective N-benzoylation of cytosine and adenine bases in mucleosides with N-benzoyltetrazole

Tetrahedron Letters

Volumn 38, Issue 51, 1997, Pages 8811-8814

  Bhat, Balkrishen ^a   Sanghvi, Yogesh S ^a  

^a ISIS PHARMACEUTICALS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADENINE DERIVATIVE; CYTOSINE DERIVATIVE; NUCLEIC ACID BASE; NUCLEOTIDE;

ARTICLE; DNA SYNTHESIS; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030779557     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10423-3     Document Type: Article

References (28)

1. A portion of this work was reported briefly at 213th National Meeting of American Chemical Society, San Francisco, California, April 1997; CARB 105.
2. Selected books and review articles: (a) Uhlmann, E.; Peyman, A. Chem. Rev. 1990, 90, 543
3. (b) Therapeutic Applications of Oligonucleotides; Crooke, S. T.; Ed; R.G. Lands Co.; Austin, TX, 1995.
4. (c) Antisense Research and Applications; Crooke, S. T., Lebleu, B., Eds. ; CRC Press: Boca Raton, FL, 1993.
5. (d) Methods in Molecular Medicine: Antisense Therapeutics; Agarwal, S., Ed.; Humana Press Inc., Totowa, NJ, 1996.
6. (e) Bioorganic Chemistry: Nuckic Acids; Hecht, S. M., Ed.; Oxford University Press: New York, 1996.
7. (f) Perspective in Drug Discovery and Design: Antisense therapeutics and Prospects; Trainer, G. L., Ed.; ESCOM; Leiden, The Netherlands, 1996.
8. (g) Crooke, S. T.; Bennett, C. F. Annu. Rev. Pharmacol. Toxicol. 1996, 36, 107.
9. (h) Matteucci, M. D.; Bischofberger, N. Annu. Rep. Med. Chem. 1991, 26, 287.
10. (a) Sanghvi, Y. S. ; Cook, P. D. In Nucleosides and Nucleotides as Antitumor and Antiviral Agents; Chu, C.K., Baker, D. C., Eds., Plenum Press: New York, 1993, p 311.
11. (b) Sanghvi, Y. S.; Cook, P.D. In Carbohydrate Modifications in Antisense Research; Sanghvi, Y. S., Cook, P.D., Eds.; ACS symposium Series 580; American Chemical Society: Washington, DC, 1994; p 1-22 and refrences therein.
12. Sonveaux, E., In Methods in Molecular Biology: Protocols for Oligonucleotide Conjugates; Agarwal, S., Ed.; Humana Press Inc., Totowa, NJ, 1994, 1 and the refrences therein.
13. Schaller, H., Weiraan, G., Lerch, B. and Khorana, H. G. J. Am .Chem. Soc. 1963, 85, 3821.
14. Ti, G. S.; Gaffney, B. L. and Jones, R. A. J. Am. Chem. Soc. 1982, 104, 1316.
15. Kierzek, R. Nucleosides Nucleotides, 1985, 4, 641.
16. Sekine, M. Natural Products Letters, 1992, 1, 135.
17. Sinha, N. D.; Davis, P.; Schultze, L. M. and Upadya, K. Tetrahedron Lett. 1995, 36, 9277.
18. (a)Hayakawa, Y.; Kato, H.; Uchiyama, Kajino, H.; Noyori, R. J. Org. Chem. 1986, 51, 2400.
19. (b) Hayakawa, Y.; Kato, H.; Noyori, R. Tetrahedron Lett. 1985, 26, 6505.
20. (c) Hayakawa, Y.; Wakahayashi, S.; Kato, H.; Noyori, R. J. Am. Chem. Soc. 1990, 112, 1691.
21. (a) Bhat, B.; Leonard, N. J.; Robinson, H.; Wang, A. H.-J. J. Am. Chem. Soc. 1996, 118, 10744.
22. (b) Bhat, B.; Neelima.; Léonard, N.J.; Robinson, H.; Wang, A. H.-J. J. Am. Chem. Soc. 1996, 118, 3065.
23. (c) Leonard, N. J.; Neelima. Nucleosides Nucleotides 1996, 15, 1369.
24. (d) Pirrung, M. C.; Fallon, L.; Lever, D. C; Shuey, S. W. J. Org. Chem. 1996, 61, 2129.
25. Bhat, B.; Swayze, E. E.; Wheeler, P.; Dimock, S.; Perbost, M.; Sanghvi, Y. S. J. Org. Chem. 1996, 61, 8186.
26. Stawinski, J.; Hozumi, T.; Narang, S. A. J. Chem. Soc. 1976, 243.
27. Krotz, A. H.; Klopchin, P.; Walker, K. L.; Srivastsa, G. S.; Cole, D. L.; Ravikumar, V. T. Tetrahedron Lett. 1997, 38, 3875.
28. +) 175.0620, found 175.0627.