A simple solution to the age old problem of regioselective functionalization of guanine: First practical synthesis of acyclic N9- and/or N7-guanine nucleosides starting from N2,N9-diacetylguanine

Journal of Organic Chemistry

Volumn 64, Issue 13, 1999, Pages 4665-4668

  Singh, Dharmendra ^a   Wani, Mukesh J ^a   Kumar, Ashok ^a  

^a LUPIN LIMITED   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACICLOVIR; ACID; GANCICLOVIR; GUANINE; GUANINE DERIVATIVE; GUANOSINE;

ALKYLATION; ARTICLE; CATALYSIS; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033603562     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982304y     Document Type: Article

References (37)

1. (a) Kjellberg, J.; Johansson, N. G. Tetrahedron 1988, 42, 6541.
2. (b) Kjellberg, J.; Johansson, N. G. Nucleosides Nucleotides 1989, 8, 225 and references therein.
3. (a) Ellion, G. B.; Furman, P. A.; Fyfe, J. A.; de Miranda, P.; Beauchamp, L. M. Schaeffer, H. J. Proc. Natl. Acad. Sci. U.S.A. 1977, 74, 5716.
4. (b) Schaeffer, H. J.; Beauchamp, L. M.; de Miranda, P.; Elion, G. B.; Bauer, D. J.; Collins, P. Nature (London) 1978, 272, 583.
5. (c) Beauchamp, L. M.; Dolmatch, B. L.; Schaefier, H. J.; Collins, P.; Bauer, D. J.; Kelter, P. M.; Fyfe, J. A. J. Med. Chem. 1986, 28, 982.
6. (d) Schaeffer, H. J. Ger. Patent 2539963, 1974.
7. Hua, M.; Korkowski, P. M.; Vince, R. J. Med. Chem. 1987, 30, 198.
8. Lin, T.-S.; Liu, M.-C. Tetrahedron Lett. 1984, 25, 611.
9. Robins, M. J.; Zou, R.; Hanske, F.; Madej, D.; Tyrrell, D. L. J. Nucleosides Nucleotides 1989, 8, 725.
10. Boryski, J.; Manikowski, A. Nucleosides Nucleotides 1995, 14, 287.
11. Matsumoto, H.; Kaneko, C.; Yamada, K.; Takeuchi, T.; Mori, T.; Mizuno, Y. Chem. Pharm. Bull. 1988, 36, 1153.
12. (a) Ogilvie, K. K.; Cheriyan, U. O.; Radatus, B. K.; Smith, K. O.; Galloway, K. S.; Kennell, W. L. Can. J. Chem. 1982, 60, 3005.
13. (b) Ashton, W. T.; Karkas, J. D.; Field, A. K.; Tolman, R. L. Biochem. Biophys. Res. Commun. 1982, 108, 1716.
14. (c) Martin, J. C.; Dvorak, C. A.; Smee, D. F.; Mathews, T. R.; Verheyden, J. P. H. J. Med. Chem. 1983, 26, 759.
15. Hirsch, M. S.; Kaplan J. C. In Virology, Vol. 1; Fields, B. N., Knipe, D. M., Chanock, R. M., Hirsch, M. S., Melnick, J. L., Monath, T. P., Roizman, B., Eds.; Raven: New York, 1990; p 441.
16. Jahne, G.; Kroha, H.; Muller, A.; Helsberg, M.; Winkler, I.; Gross, G.; Scholl, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 562.
17. Harnden, M. R.; Jarvest, R. L.; Bacon, T. H.; Boyd, M. R. J. Med. Chem. 1987, 30, 1636 and references therein.
18. Geen, G. R.; Grinter, T.; Kincey, P, M.; Jarvest, R. L. Tetrahedron 1990, 46, 6903.
19. Zou, R.; Robins, M. J. Can. J. Chem. 1987, 65, 1436 and references therein.
20. MacCoss, M.; Chen, A.; Tolman, R. L. Tetrahedron Lett. 1985, 26, 4287.
21. (a) Vorbruggen, H.; Krolikiewicz, K.; Bennua, B. Chem. Ber. 1981, 114, 1234.
22. (b) Vorbruggen, H. Acta Biochim. Pol. 1996, 43, 25.
23. (a) Dudycz, L. W.; Wright, G. E. Nucleosides Nucleatides 1984, 3, 33.
24. (b) Wright, G. E.; Dudycz, L. W. J. Med. Chem. 1984, 27, 175.
25. Garner, P.; Ramakanth, S. J. Org. Chem. 1988, 53, 1294.
26. (a) Sheppard, T. L.; Rosemblatt, A. T.; Breslow, R. J. Org. Chem. 1994, 59, 7243.
27. (b) Chamberlain, S. D.; Biron, K. K.; Dornsife, R. E.; Averatt, D. R.; Beauchamp, L.; Koszalka, G. W. J. Med. Chem. 1994, 37, 1371.
28. (a) Rao, T. S.; Durland, R. H.; Revenkar, G. R. J. Hetrocycl. Chem. 1994, 31, 935.
29. (b) Hunziker, J.; Priestley, E. S.; Brunar, H.; Dervan, P. B. J. Am. Chem. Soc. 1995, 117, 2661.
30. Robins, M. J.; Zou, R.; Guo, Z.; Wruk, S. F. J. Org. Chem. 1996, 61, 9207.
31. Kumar, A.; Singh, D.; Wani, M. J.; Joshi, N. S.; Thombre, P. S.; Rawat, A. S. European Patent 806,425 A1, 1996.
32. 3).
33. 9 = 45/55 (Boryski J.; Golankiewicz, B. Nucleosides Nucleotides 1989, 8, 529.)
34. 9 transformation.
35. Boryski, J. Nucleosides Nucleotides 1996, 15(1-3), 771 and references therein.
36. 9 isomer with its kinetically controlled counterpart (13) was established by repeated experimentation and continuous monitoring of the reaction starting from zero hour.
37. 2-CO).