Synthesis of Acyclonucleoside Derivatives of 5-Alkoxymethyluracils

(Note: The full text of this document is currently only available in the PDF Version )

Ahmed El-Sayed Abdel-Megied


Abstract

The silyl derivatives 3ac were treated with ethoxymethyl chloride (4a) or (2-acetoxyethoxy)methyl bromide (4b) to afford 5ac and 6ac, respectively; 7ac were prepared by treating 6ac with MeONa; treatment of 5ac or 6ac with tris(1H-1,2,4-triazole-1-yl)phosphine oxide and subsequent reaction of 8ac and 9ac with ammonia in dioxane to give 10ac and 11ac; ammonolysis of 11ac yielded the hydroxyalkyl derivatives 12ac.


References

  1. F. Barre-Sinoussi, J. C. Chermann, F. Rey, M. T. Chamaret, J. Grust, C. Daugnet, C. Axler-Blin, F. Vezinet-Brun, C. Rouzioux, W. Rozenbaum and L. Montagnier, Science, 1983, 220, 868 CAS.
  2. R. C. Gallo, S. Z. Salahuddin, M. Popovic, G. M. Shearer, M. Kaplan, B. F. Haynes, T. J. Palker, R. Redfield, J. Oleske, B. Safai, G. White, P. Foster and P. D. Markham, Science, 1984, 224, 500 CAS.
  3. H. Mitsuya, K. J. Weinhold, P. A. Furman, M. H. St. Clair, S. N. Lehrman, R. C. Gallo, D. Bolognesi, D. W. Barry and S. Broder, Proc. Natl. Acad. Sci. USA, 1985, 82, 7096 CAS.
  4. H. Tanaka, M. Baba, H. Hayakawa, T. Sakamaki, T. Miyasaka, M. Ubasawa, H. Takashima, K. Sekiya, I. Nitta, S. Shigeta, R. T. Walker, J. Balzarini and E. De Clercq, J. Med. Chem., 1991, 34, 349 CrossRef CAS.
  5. S. Yuasa, Y. Sadakata, H. Takashima, K. Sekiya, N. Inoue, M. Ubasawa and M. Baba, MKC-442, Mol. Pharmacol., 1993, 44, 895 Search PubMed.
  6. M. Baba, H. Tanaka, T. Miyasaka, S. Yuasa, M. Ubasawa, R. T. Walker and E. De Clercq, Nucleosides Nucleotides, 1995, 14, 575 CAS.
  7. H. J. Schaeffer, L. Beauchamp, P. de Miranda, G. B. Elion, D. J. Bauer and P. Collins, Nature, 1987, 272, 583.
  8. R. E. Cline, R. M. Fink and K. Fink, J. Am. Chem. Soc., 1959, 81, 2521 CrossRef CAS.
  9. G. L. Bubbar and V. S. Gupta, Can. J. Chem., 1970, 48, 3147 CAS.
  10. M. S. Motawia, A. E.-S. Abdel-Megied and E. B. Pedersen, Acta Chem. Scand., 1992, 46, 71.
  11. E. Wittenburg, Z. Chem., 1964, 4, 303 CAS.
  12. M. J. Robins and P. W. Hatfield, Can. J. Chem., 1982, 60, 547 CAS.
  13. A. Kraszewski and J. Stawinski, Tetrahedron Lett., 1980, 21, 2935 CrossRef.
Click here to see how this site uses Cookies. View our privacy policy here.