1887
Volume 2012, Issue 1
  • EISSN: 2223-506X

Abstract

Abstract

: Organophosphorus compounds have important industrial and biomedical applications as pharmaceutical and agrochemical agents, as well as transition state analogs for the production of monoclonal antibodies.

: Two diastereomers of a 6-membered ring, cyclic phenyl phosphonate were synthesized in 8 steps from 1,3-butanediol.

: The stereochemistry of the diastereomers was elucidated on the basis of P NMR signals, together with H NMR nuclear Overhauser effects (NOE) difference experiments.

: Such cyclic phosphonates may have utility serving as transition state analogs for the production of monoclonal antibodies.

Loading

Article metrics loading...

/content/journals/10.5339/connect.2012.2
2012-03-05
2024-11-13
Loading full text...

Full text loading...

/deliver/fulltext/connect/2012/1/connect.2012.2.html?itemId=/content/journals/10.5339/connect.2012.2&mimeType=html&fmt=ahah

References

  1. McReynolds, M.D., Dougherty, J.M., & Hanson, P.R. (2004). Chem. Rev., 104:, 2239.
    [Google Scholar]
  2. Kafarski, P., & Lejczak, B. (2001). Curr. Med. Chem. Anticancer Agents, 1:, 301.
    [Google Scholar]
  3. Colvin, O.M. (1999). Curr. Pharm. Des., 5:, 555.
    [Google Scholar]
  4. Mader, M.M., & Bartlett, P.A. (1997). Chem. Rev., 97:, 1281.
    [Google Scholar]
  5. Kafarski, P., & Lejczak, B. (1991). Phosphorus, Sulfur, Silicon Relat. Elem., 63:, 193.
    [Google Scholar]
  6. Zon, G. (1982). Cyclophosphamide analogues. Prog. Med. Chem., 19:, 205246.
    [Google Scholar]
  7. Nagarajan, R., Kwon, K., Nawrot, B., Stec, W.J., & Stivers, J.T. (2005). Biochem., 44:, 11476.
    [Google Scholar]
  8. Franz, J.E., Mao, M.K., & Sikorski, J.A. (1997). Glyphosate: A Unique Global Herbicide. American Chemical Society, Washington, DC.
    [Google Scholar]
  9. Yu, F., Lian, X., Zhao, J., Yu, Y., & Ma, S. (2009). J. Org. Chem., 74:, 1130.
    [Google Scholar]
  10. Yu, F., Lian, X., & Ma, S. (2007). Org. Lett., 9:, 1703.
    [Google Scholar]
  11. Stoianova, D.S., Whitehead, A., & Hanson, P.R. (2005). J. Org. Chem., 70:, 5880.
    [Google Scholar]
  12. Cao, Y., Hidaka, A., Tajima, T., & Fuchigami, T. (2005). J. Org. Chem., 70:, 9614.
    [Google Scholar]
  13. Stoianova, D.S., & Hanson, P.R. (2001). Org. Lett., 3:, 3285.
    [Google Scholar]
  14. Darrow, J.W., & Drueckhammer, D.G. (1994). J. Org. Chem., 59:, 2976.
    [Google Scholar]
  15. Harvey, T.C., Weiler, L., & Withers, S.G. (1997). J. Org. Chem., 62:, 6722.
    [Google Scholar]
  16. Pungente, M.D., Weiler, L., & Ziltener, H.J. (2002). Can. J. Chem., 80:, 1643.
    [Google Scholar]
  17. Jacobs, J.W. Ph.D. Thesis, University of California, Berkeley, 1990.
  18. Napper, A.D., Benkovic, S.J., Tramontano, A., & Lerner, R.A. (1987). Science, 237:, 1041.
    [Google Scholar]
  19. Pungente, M.D., & Weiler, L. (2001). Org. Lett., 3:, 643.
    [Google Scholar]
  20. Jones, G.H., Hamamura, E.K., & Moffatt, J.G. (1968). Tet. Lett., 5731.
    [Google Scholar]
  21. Darrow, J.W., & Drueckhammer, D.G. (1996). Bioorg. Med. Chem., 4:, 1341.
    [Google Scholar]
  22. Hanessian, S., Galeotti, N., Rosen, P., Oliva, G., & Babu, S. (1994). Bioorg. Med. Chem. Lett., 4:, 2763.
    [Google Scholar]
  23. Gorenstein, D.G. (1987). Chem. Rev., 87:, 1047.
    [Google Scholar]
  24. Chang, J.W., & Gorenstein, D.G. (1987). Tetrahedron, 43:, 5187.
    [Google Scholar]
  25. Perrin, D.D., & Armarego, W.L.F. (1988). Purification of Laboratory Chemicals. 3rd ed., Permagon, New York, NY.
    [Google Scholar]
  26. Still, W.C., Kahn, M., & Mitra, A. (1978). J. Org. Chem., 43:, 2923.
    [Google Scholar]
/content/journals/10.5339/connect.2012.2
Loading
/content/journals/10.5339/connect.2012.2
Loading

Data & Media loading...

  • Article Type: Research Article
Keyword(s): 6-memberedCyclic phosphonatesNOE and stereochemistry
This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error