Efficient removal of sugar O-tosyl groups and heterocycle halogens from purine nucleosides with sodium naphthalenide

Tetrahedron

Volumn 53, Issue 18, 1997, Pages 6295-6302

  Lewandowska, Elzbieta ^a   Neschadimenko, Vladimir ^a   Wnuk, Stanislaw F ^a   Robins, Morris J ^a  

^a Brigham Young University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE; PURINE NUCLEOSIDE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030894640     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00313-X     Document Type: Article

References (30)

1. Nucleic Acid Related Compounds. 98. Part 97 is: Wnuk, S. F.; Yuan, C.-S.; Borchardt, R. T.; Balzarini, J.; De Clercq, E.; Robins, M. J. J. Med. Chem., in press.
2. On faculty leave from the Department of Chemistry, University of Agriculture, Poznan, Poland.
3. (a) Ebel, H. F.; Lüttringhaus, A. In Houben-Weyl, 4th ed., Vol. 13/1; Müller, E., Ed.; Thieme: Stuttgart, 1970; pp 255-725.
4. (b) Wardell, J. L. In Comprehensive Organometallic Chemistry, Vol. 1; Wilkinson, G.;Stone, F. G. A; Abel, E. W., Eds.; Pergamon Press: Oxford, 1982; pp 43-120.
5. (c) Molander, G. A.; Harris, C. R. In Encyclopedia of Reagents for Organic Synthesis, Vol. 7; Paquette, L. A., Ed.; John Wiley & Sons: Chichester, 1995; pp 4602-4604.
6. Garst, J. F. Acc. Chem. Res. 1971, 4, 400.
7. (a) Closson, W. D.; Wriede, P.; Bank, S. J. Am. Chem. Soc. 1966, 88, 1581.
8. (b) Closson, W. D.; Ganson, J. R.; Rhee, S. W.; Quaal, K. S. J. Org. Chem. 1982, 47, 2476.
9. Ji, S.; Gortler, L. B.; Waring, A.; Battisti, A.; Bank, S.; Closson, W. D.; Wriede, D. J. Am. Chem. Soc. 1967, 89 5311.
10. Jarrell, H. C.; Ritchie, R. G. S.; Szarek, W. A.; Jones, J. K. N. Can. J. Chem. 1973, 51, 1767.
11. Srivastava, P. C.; Robins, R. K.; Meyer, R. B., Jr. In Chemistry of Nucleosides and Nucleotides, Vol. 1; Townsend, L. B., Ed.; Plenum Press: New York, 1988; pp 113-281.
12. 8
13. Azuma, T; Yanagida, S.; Sakurai, H. Synth. Commun. 1982, 12, 137.
14. Philips, K. D.; Horwitz, J. P. J. Org. Chem. 1975, 40, 1856.
15. (a) Greene, G. L.; Letsinger, R. L. Tetrahedron Lett. 1975, 2081.
16. (b) Letsinger, R. L.; Finnan, J. L. J. Am. Chem. Soc. 1975, 97, 7197.
17. Wagner, D.; Verheyden, J. P. H.; Moffatt, J. G. J. Org. Chem. 1974, 39, 24.
18. Jenkins, I. D.; Verheyden, J. P. H.; Moffatt, J. G. J. Am. Chem. Soc. 1976, 98, 3346.
19. Herdewijn, P. Tetrahedron 1989, 45, 6563.
20. Robins, M. J.; Fouron, Y.; Mengel, R. J. Org. Chem. 1974, 39, 1564.
21. Herdewijn, P.; Van Aeschot, A.; Kerremans, L. Nucleosides Nucleotides 1989, 8, 65.
22. Nair, V.; Young, D. A.; De Silvia, R., Jr. J. Org. Chem. 1987, 52, 1344.
23. (a) Gerster, J. F.; Jones, J. W.; Robins, R. K. J. Org. Chem. 1963, 28, 945.
24. (b) Robins, M. J.; Uznanski, B. Can. J. Chem. 1981, 59, 2601.
25. Ti, G. S.; Gaffney, B. L.; Jones, R. A. J. Am. Chem. Soc. 1982, 104, 1316.
26. Kuhn, R.; Jahn, W. Chem. Ber. 1965, 98, 1699.
27. David, S.; Fischer, J.-C. Bull. Soc. Chim. Fr. 1972, 3610.
28. Levene, P. A.; Tipson, R. S. J. Biol. Chem. 1934, 106, 113.
29. Beaton, G.; Jones, A. S.; Walker, R. T. Tetrahedron 1988, 44, 6419.
30. Maguire, A. R.; Meng, W.-D.; Roberts, S. M.; Willetts, A. J. J. Chem. Soc., Perkin Trans. 1 1993, 1795.