Convenient synthesis of C-aza-2,3-dideoxynucleosides

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

Atsuya Momotake, Hideo Togo and Masataka Yokoyama


Abstract

1-Aryl-1,2,3,4-tetradeoxy-1,4-imino-D-pentitols 5 and 9f are easily synthesized from N-Boc-L-pyroglutamate 1 via a successive procedure involving regioselective ring-opening, recyclization with dehydration, stereoselective reduction, and reduction of the ester group. Their structures are determined mainly by X-ray crystallography and NMR measurements. Their bioassay is also described.


References

  1. (a) H. Mitsuya and S. Broder, Proc. Natl. Acad. Sci. USA, 1986, 83, 1911 CAS; (b) J. Balzarini, B. Masanori, R. Pauwels, P. Herdewijn, S. G. Wood, M. J. Robins and E. De Clercq, Mol. Pharmacol, 1988, 33, 243 Search PubMed; (c) E. De Clercq, A. van Aerschot, P. Herdewijn, M. Baba, R. Panwels and J. Balzarini, Nucleosides, Nucleotides, 1989, 8, 659.
  2. H. Mitsuya, R. Yarochan and S. Broder, Science, 1990, 249, 1533 CrossRef.
  3. (a) C. H. Wong, L. Provencher, J. A. Porco Jr., S. H. Jung, Y. F. Wang, L. Chen, R. Wang and D. H. Steensma, J. Org. Chem., 1995, 60, 1492 CrossRef CAS; (b) G. C. Look, C. H. Fotsch and C. H. Wong, Acc. Chem. Res., 1993, 26, 182 CrossRef CAS.
  4. C-Azanucleosides: (a) G. D. Kini and W. J. Hennen, J. Org. Chem., 1986, 51, 4336; (b) G. Just and P. Donnini, Can. J. Chem., 1977, 55, 2998 CAS; (c) B. A. Horenstein, R. F. Zabinski and V. L. Schramm, Tetrahedron Lett., 1993, 34, 7213 CrossRef CAS; (d) R. H. Furneaux, G. Limberg, P. C. Tyler and V. L. Schramm, Tetrahedron, 1997, 53, 2915 CrossRef CAS; (e) L. Deng, O. D. Scharer and G. L. Verdine, J. Am. Chem. Soc., 1997, 119, 7865 CrossRef CASN-Azanucleosides: (f) E. J. Reist, D. E. Gueffroy, R. W. Blackford and L. Googman, J. Org. Chem., 1966, 31, 4025 CAS; (g) B. Huang, B. Chen and Y. Yui, Synthesis, 1993, 769 CrossRef CAS; (h) K. H. Altman, S. M. Freier, U. Piels and T. Winkler, Angew. Chem., Int. Ed. Engl., 1994, 33, 1654 CrossRef; (i) G. Rassu, L. Pinna, P. Spanu, F. Ulgheri and G. Cashiragi, Tetrahedron Lett., 1994, 35, 4019 CrossRef CAS.
  5. (a) A. Momotake, J. Mito, K. Yamaguchi, H. Togo and M. Yokoyama, J. Org. Chem., 1998, 63, 7207 CrossRef CAS; (b) M. Yokoyama, T. Ikeue, Y. Ochiai, A. Momotake, K. Yamaguchi and H. Togo, J. Chem. Soc., Perkin Trans. 1, 1998, 2185 RSC.
  6. (a) R. B. Silverman and M. A. Levy, J. Org. Chem., 1980, 45, 815 CrossRef CAS; (b) D. L. Fiynn, R. E. Zelleand and P. A. Grieco, J. Org. Chem., 1983, 48, 2424 CrossRef CAS.
  7. (a) T. Ohta, A. Hosoi, T. Kimura and S. Nozoe, Chem. Lett., 1987, 2091 CAS; (b) J. Ezquerra, J. de Mendoza, C. Pedregal and C. Ramirez, Tetrahedron Lett., 1992, 33, 5589 CrossRef CAS; (c) A. Schoenfelder and A. Mann, Synth. Commun., 1989, 19, 3485; (d) M. T. Molina, C. del Valle, A. M. Escribano, J. Ezquerra and C. Pedregal, Tetrahedron, 1993, 49, 3801 CrossRef CAS.
  8. M. Yokoyama, A. Shimura, A. Momotake and H. Togo, Synthesis, 1999, 495.
  9. T. Imamoto, N. Takiyama, K. Nakamura, T. Hatajima and Y. Kamiya, J. Am. Chem. Soc., 1989, 111, 4392 CrossRef CAS.
  10. R. O. Hutchins, W.-Y. Su, R. Sivakumar, F. Cistone and Y. P. Stercho, J. Org. Chem., 1983, 48, 3412 CrossRef CAS.
  11. M. B. Eleveld, H. Hogeveen and E. P. Schudde, J. Org. Chem., 1986, 51, 3635 CrossRef CAS.
  12. A. L. Gemal and J.-L. Luche, J. Am. Chem. Soc., 1981, 103, 5454 CrossRef CAS.
  13. R. Pauwels, J. Balzarini, M. Baba, R. Snoeck, D. Schols, P. Herdewijn, J. Desmyter and E. De Clercq, J. Virol. Methods, 1988, 20, 309 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.