Protection of Phosphoric and Related Acids

  • F. Eckstein


The central role played by nucleic acids in the living cell continues to stimulate considerable research into the functions and structure of these polymers, and various methods of synthesis of low molecular weight oligomers and analogues of nucleic acids have been described. These have entailed the use of protecting groups, not only for the shielding of the sugar moiety and amino function in the bases, but also for mono- and di-esters of phosphoric acid. It is therefore not surprising that many of the recent advances in protecting oxyacids of phosphorus have taken place in this area of chemistry. This brief review assumes acquaintance with the articles by J. J. Fox [1] and J. F. W. McOmie [2], and covers the more recent developments in this field. Emphasis is placed on protecting groups which have either found wider application, or show new approaches to the problem.


Phosphonic Acid Tetrahedron Letter Relate Acid Carboxylic Acid Ester Phosphate Monoester 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


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  1. 1.
    T. UEDA and J. J. FOX, Adv. Carbohydrate Chem., 22, 307 (1967).CrossRefGoogle Scholar
  2. 2.
    J. F. W. MCOMIE, Adv. Org. Chem., 3, 191 (1963).Google Scholar
  3. 3.
    G. M. TENER, J. Amer. Chem. Soc., 83, 159 (1961).CrossRefGoogle Scholar
  4. 4.
    H. G. KHORANA, Pure Appl. Chem., 17, 349 (1968).CrossRefGoogle Scholar
  5. 5.
    E. OHTSUKA, M. W. MOON, and H. G. KHORANA, J. Amer. Chem. Soc., 87, 2956 (1965).CrossRefGoogle Scholar
  6. 6.
    R. H. SYMONS, Biochim. Biophys. Acta, 209, 296 (1970).Google Scholar
  7. 7.
    W. FREIST and F. CRAMER, Chem. Ber., 103, 3122 (1970).CrossRefGoogle Scholar
  8. 8.
    S. A. NARANG, O. S. BHANOT, J. GOODCHILD, and R. WIGHTMAN, Chem. Comm., 91 (1970).Google Scholar
  9. 9.
    S. A. NARANG, O. S. BHANOT, J. GOODCHILD, J. MICHWIEWICZ, R. H. WIGHTMAN, and S. K. DHEAR, Chem. Comm., 516 (1970).Google Scholar
  10. 10.
    T. HATA, Y. MUSHIKA, and T. MUKAIYAMA, Tetrahedron Letters, 3505 (1970).Google Scholar
  11. 11.
    F. CRAMER and K. H. SCHEIT, Annalen, 679, 150 (1964).Google Scholar
  12. 12.
    F. CRAMER, H. P. BAER, H. J. RHAESE, W. SAENGER, K. H. SCHEIT, G. SCHNEIDER, and J. TENNIGKEIT, Tetrahedon Letters, 1039 (1963).Google Scholar
  13. 13.
    H. A. C. MONTGOMERY and J. H. TURNBULL, J. Chem. Soc., 1963 (1958).Google Scholar
  14. 14.
    J. G. MOFFATT, Canad. J. Chem., 42, 599 (1964).CrossRefGoogle Scholar
  15. 15.
    G. M. BLACKBURN, M. J. BROWN, and M. R. HARRIS, J. Chem. Soc. (C), 2438 (1967).Google Scholar
  16. 16.
    T. WIELand and R. LAMBERT, Chem. Ber., 89, 2476 (1956).CrossRefGoogle Scholar
  17. 17.
    A. F. COOK, M. J. HOLMAN, and A. L. NUSSBAUM, J. Amer. Chem. Soc., 91, 6479 (1969).CrossRefGoogle Scholar
  18. 18.
    H. SOMMER, Thesis, Braunschweig, 1971.Google Scholar
  19. 19.
    F. KATHAWALA and F. CRAMER, Annalen, 712, 195 (1968).Google Scholar
  20. 20.
    P. J. BUNYAN and J. I. G. CADOGAN, J. Chem. Soc., 1304 (1962).Google Scholar
  21. 21.
    E. OHTSUKA, K. MURAO, M. UBASAWA, and M. IKEHARA, J. Amer. Chem. Soc., 92, 3441 (1970).CrossRefGoogle Scholar
  22. 22.
    E. OHTSUKA, M. UBASAWA, and M. IKEHARA, J. Amer. Chem. Soc., 92, 5507 (1970).CrossRefGoogle Scholar
  23. 23.
    R. B. WOODWARD, K. HEUSLER, J. GOSTELI, P. NAEGELI, W. OPPOLZER, R. RAMAGE, S. RANGANATHAN, and H. VORBRüGGEN, J. Amer. Chem. Soc., 88, 852 (1966).CrossRefGoogle Scholar
  24. 24.
    F. ECKSTEIN, Chem. Ber., 100, 2236 (1967).CrossRefGoogle Scholar
  25. 25.
    A. FRANKE, F. ECKSTEIN, K. H. SCHEIT, and F. CRAMER, Chem. Ber., 101, 944 (1968).CrossRefGoogle Scholar
  26. 26.
    A. J. KIRBY and A. G. VARVOGLIS, Chem. Comm., 406 (1967).Google Scholar
  27. 27.
    D. L. MILLER and T. UKENA, J. Amer. Chem. Soc., 91, 3050 (1969).CrossRefGoogle Scholar
  28. 28.
    V. M. CLARK, J. B. HOBBS, and D. W. HUTCHINSON, Chem. Comm., 339 (1970).Google Scholar
  29. 29.
    F. ECKSTEIN and I. RIZK, Chem. Ber., 102, 2362 (1969).CrossRefGoogle Scholar
  30. 30.
    T. NEILSON, Chem. Comm., 1139 (1969).Google Scholar
  31. 31.
    A. FRANKE, K. H. SCHEIT, and F. ECKSTEIN, Chem. Ber., 101, 2998 (1968).CrossRefGoogle Scholar
  32. 32.
    H. LüTGE, STöCKHEIM, Personal Communication.Google Scholar
  33. 33.
    K. H. SCHEIT, Tetrahedron Letters, 3243 (1967).Google Scholar
  34. 34.
    R. L. LETSINGER, K. K. OGLIVIE, and P. S. MILLER, J. Amer. Chem. Soc., 91, 3360 (1969).CrossRefGoogle Scholar
  35. 35.
    G. W. GRAMS and R. L. LETSINGER, J. Org. Chem., 35, 868 (1970).CrossRefGoogle Scholar
  36. 36.
    C. B. REESE and R. SAFFBILL, Chem. Comm., 767 (1968).Google Scholar
  37. 37.
    F. ECKSTEIN, J. Amer. Chem. Soc., 92, 4718 (1970).CrossRefGoogle Scholar
  38. 38.
    A. F. COOK, J. Amer. Chem. Soc., 92, 190 (1970).CrossRefGoogle Scholar
  39. 39.
    R. S. GOODY and F. ECKSTEIN, J. Amer. Chem. Soc., 93, 6252 (1971).CrossRefGoogle Scholar
  40. 40.
    D. H. RAMMLER, L. YENGOYAN, A. V. PAUL, and P. C. BAX, Biochemistry, 6, 1828 (1967).CrossRefGoogle Scholar
  41. 41.
    A. HOLY, Tetrahedron Letters, 881 (1967).Google Scholar
  42. 42.
    G. H. JONES, and J. G. MOFFATT, J. Amer. Chem. Soc., 90, 5337 (1968).CrossRefGoogle Scholar
  43. 43.
    T. L. HULLAR, Tetrahedron Letters, 4921 (1967).Google Scholar
  44. 44.
    B. J. JASTORFF and H. HETTLER, Chem. Ber., 102, 4119 (1969).CrossRefGoogle Scholar
  45. 45.
    A. MURAYAMA, B. JASTORFF, and H. HETTLER, Angew. Chem., 82, 666 (1970);CrossRefGoogle Scholar
  46. 45a.
    A. MURAYAMA, B. JASTORFF, and H. HETTLER, Angew. Chem. Internat. Edn., 9, 640 (1970).CrossRefGoogle Scholar
  47. 46.
    T. Y. SHEN, Angew. Chem., 82, 730 (1970);CrossRefGoogle Scholar
  48. 46a.
    T. Y. SHEN, Angew. Chem. Internat. Edn., 9, 678 (1970).CrossRefGoogle Scholar
  49. 47.
    R. L. LETSINGER and W. S. MUNGALL, J. Org. Chem., 35, 3800 (1970).CrossRefGoogle Scholar

Copyright information

© Plenum Publishing Company Ltd 1973

Authors and Affiliations

  • F. Eckstein
    • 1
  1. 1.Abteilung ChemieMax-Planck Institut für Experimentelle MedizinGöttingenGermany

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