Facile synthesis and conformation of 3′-O,4′-C-methyleneribonucleosides

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

Satoshi Obika, Ken-ichiro Morio, Yoshiyuki Hari and Takeshi Imanishi


Abstract

Bicyclic nucleoside analogues, 3′-O,4′-C-methyleneribonucleosides 1, including thymine, cytosine, adenine and guanine nucleobases, were conveniently synthesized from D-glucose, and the ribofuranose ring of 1 was found to exist predominantly in a S-conformation by means of 1H NMR and X-ray analysis.


References

  1. E. Uhlmann and A. Peyman, Chem. Rev., 1990, 90, 543 CrossRef CAS; S. L. Beaucage and R. P. Iyer, Tetrahedron, 1993, 49, 6123 CrossRef CAS; J. F. Milligan, M. D. Matteucci and J. C. Martin, J. Med. Chem., 1993, 36, 1923 CrossRef CAS; N. T. Thuong and C. Hélène, Angew. Chem., Int. Ed. Engl., 1993, 32, 666 CrossRef.
  2. H. Hashimoto and C. Switzer, J. Am. Chem. Soc., 1992, 114, 6255 CrossRef CAS; J. P. Dougherty, C. J. Rizzo and R. Breslow, J. Am. Chem. Soc., 1992, 114, 6254 CrossRef CAS; P. A. Giannaris and M. J. Damha, Nucleic Acids Res., 1993, 21, 4742 CrossRef CAS; R. Alul and G. D. Hoke, Antisense Res. Dev., 1995, 5, 3 Search PubMed; T. P. Prakash, K.-E. Jung and C. Switzer, Chem. Commun., 1996, 1793 RSC; T. L. Sheppard and R. Breslow, J. Am. Chem. Soc., 1996, 118, 9810 CrossRef CAS; E. R. Kandimalla, A. Manning, Q. Zhao, D. R. Shaw, R. A. Byrn, V. Sasisekharan and S. Agrawal, Nucleic Acids Res., 1997, 25, 370 CrossRef.
  3. H. C. Schröder, R. J. Suhadolnik, W. Pfleiderer, R. Charubala and W. E. G. Müller, Int. J. Biochem., 1992, 24, 55 Search PubMed.
  4. M. Wasner, R. J. Suhadolnik, S. E. Horvath, M. E. Adelson, N. Kon, M.-X. Guan, E. E. Henderson and W. Pfleiderer, Helv. Chim. Acta, 1997, 80, 1061 CAS; E. I. Kvasyuk, T. I. Kulak, O. V. Tkachenko, S. L. Sentyureva, I. A. Mikhailopulo, R. J. Suhadolnik, E. E. Henderson, S. E. Horvath, M.-X. Guan and W. Pfleiderer, Helv. Chim. Acta., 1998, 81, 1278 CAS.
  5. V. Lalitha and N. Yathindra, Curr. Sci., 1995, 68, 68 Search PubMed; H. Robinson, K.-E. Jung, C. Switzer and A. H.-J. Wang, J. Am. Chem. Soc., 1995, 117, 837 CrossRef CAS; J. Doornbos, J. A. J. den Hartog, J. H. van Boom and C. Altona, Eur. J. Biochem., 1981, 116, 403 CAS; J. Doornbos, R. Charubala, W. Pfleiderer and C. Altona, Nucleic Acids Res., 1983, 11, 4569 CAS.
  6. P. Herdewijn, Liebigs Ann. Chem., 1996, 1337 Search PubMed; E. T. Kool, Chem. Rev., 1997, 97, 1473 CrossRef CAS.
  7. S. Obika, D. Nanbu, Y. Hari, K. Morio, Y. In, T. Ishida and T. Imanishi, Tetrahedron Lett., 1997, 38, 8735 CrossRef CAS; S. Obika, D. Nanbu, Y. Hari, J. Andoh, K. Morio, T. Doi and T. Imanishi, Tetrahedron Lett., 1998, 39, 5401 CrossRef CAS; S. K. Singh, P. Nielsen, A. A. Koshkin and J. Wengel, Chem. Commun., 1998, 455 RSC; A. A. Koshkin, S. K. Singh, P. Nielsen, V. K. Rajwanshi, R. Kumar, M. Meldgaard, C. E. Olsen and J. Wengel, Tetrahedron, 1998, 54, 3607 CrossRef CAS; S. K. Singh and J. Wengel, Chem. Commun., 1998, 1247 RSC; A. A. Koshkin, P. Nielsen, M. Meldgaard, V. K. Rajwanshi, S. K. Singh and J. Wengel, J. Am. Chem. Soc., 1998, 120, 13 252 CrossRef CAS.
  8. S. Obika, K. Morio, D. Nanbu and T. Imanishi, Chem. Commun., 1997, 1643 RSC.
  9. S. Obika, K. Morio, Y. Hari and T. Imanishi, Bioorg. Med. Chem. Lett., 1999, 9, 515 CrossRef CAS.
  10. R. D. Youssefyeh, J. P. H. Verheyden and J. G. Moffatt, J. Org. Chem., 1979, 44, 1301 CrossRef CAS.
  11. H. Vorbrüggen, K. Krolikiewiczz and B. Bennua, Chem. Ber., 1981, 114, 1234 CrossRef; H. Vorbrüggen and G. Höfle, Chem. Ber., 1981, 114, 1256 CrossRef.
  12. Measured in (CD3)2SO: T.-S. Lin, J.-H. Yang, M.-C. Liu, Z.-Y. Shen, Y.-C. Cheng, W. H. Prusoff, G. I. Birnbaum, J. Giziewicz, I. Ghazzouli, V. Brankovan, J.-S. Feng and G.-D. Hsiung, J. Med. Chem., 1991, 34, 693 Search PubMed.
  13. T. L. Sheppard, A. T. Rosenblatt and R. Breslow, J. Org. Chem., 1994, 59, 7243 CrossRef CAS.
  14. C. Altona and M. Sundaralingam, J. Am. Chem. Soc., 1973, 95, 2333 CrossRef CAS; C. Altona, Recl. Trav. Chim. Pays-Bas, 1982, 101, 413 CAS; F. A. A. M. de Leeuw and C. Altona, J. Chem. Soc., Perkin Trans. 2, 1982, 375 RSC.