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Preparation of specifically dideuterated octadecanoates and oxooctadecanoates

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Lipids

Abstract

Sixteen methylgem dideuterooctadecanoates with two deuterium atoms at positions 2- to 17- and seven oxo esters, 8-oxooctadecanoate-5,5-d 2, 8-oxooctadecanoate-11,11-d 2, 11-oxooctadecanoate-8,8-d 2, 11-oxooctadecanoate-14,14-d 2, 12-oxooctadecanoate-9,9-d 2, 7-oxooctadecanoate-10,10-d 2 and 13-oxooctadecanoate-16,16-d 2 with two deuteriums on the carbon γ to the oxo group, have been synthesized. Two principal methods of introducing deuterium were used: preparation of 2,2-dideutero acids by exchange with deuterium oxide followed by chain extension giving dideuteroxooctadecanoates, which were then reduced, as tosylhydrazones, with sodium cyanoborohydride to dideuterooctadecanoates and stepwise introduction by reduction of oxooctadecanoates with sodium borodeuteride, formation of tosylate or mesylate, reduction with lithium aluminium deuteride to tetradeuterooctadecanol and oxidation to dideuterooctadecanoic acid.

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References

  1. Tulloch, A.P., and M. Mazurek, J. Chem. Soc. Chem. Commun. 692 (1973).

  2. Tulloch, A.P., and M. Mazurek, Lipids 11:228 (1976).

    CAS  Google Scholar 

  3. Stockton, G.W., C.F. Polnaszek, L.C. Leitch, A.P. Tulloch, and I.C.P. Smith, Biochem. Biophys. Res. Comm. 60:844 (1974).

    Article  PubMed  CAS  Google Scholar 

  4. Stockton, G.W., C.F. Polnaszek, A.P. Tulloch, F. Hasan, and I.C.P. Smith, Biochemistry 15:954 (1976).

    Article  PubMed  CAS  Google Scholar 

  5. Dinh-Nguyen, Nguyen, Arkiv Kemi 28:289 (1968).

    Google Scholar 

  6. Fore, S.P., R.L. Holmes, and W.G. Bickford, JAOCS 37:490 (1960).

    CAS  Google Scholar 

  7. Hünig, S., and W. Lendle, Chem. Ber. 93:912 (1960).

    Google Scholar 

  8. Hünig, S., E. Lücke, and E. Benzing, Ibid. 91:129 (1958).

    Google Scholar 

  9. Hünig, S., and H.J. Buysch, Ibid. 100:4010 (1967).

    Google Scholar 

  10. Tulloch, A.P., J.F.T. Spencer, and P.A.J. Gorin, Can. J. Chem. 40:1326 (1962).

    Article  CAS  Google Scholar 

  11. Crossland, R.K., and K.L. Servis, J. Org. Chem. 35:3195 (1970).

    CAS  Google Scholar 

  12. Williams, H.R., and H.S. Mosher, J. Amer. Chem. Soc. 76:2984 (1954).

    Article  CAS  Google Scholar 

  13. Baumann, W.J., and H.K. Mangold, J. Org. Chem. 29:3055 (1964).

    CAS  Google Scholar 

  14. Spener, F., and H.K. Mangold, Chem. Phys. Lipids 11:215 (1973).

    Article  CAS  Google Scholar 

  15. Bowman, R.E., and W.D. Fordham, J. Chem. Soc. 3945 (1952).

  16. Cochrane, C.C., and H.J. Harwood, J. Org. Chem. 26:1278 (1961).

    Article  CAS  Google Scholar 

  17. Hutchins, R.O., C.A. Milewski, and B.E. Maryanoff, J. Amer. Chem. Soc. 95:3662 (1973).

    Article  CAS  Google Scholar 

  18. Atkinson, J.G., J.J. Csakvary, G.T. Herbert, and R.S. Stuart, Ibid. 90:498 (1968).

    Article  CAS  Google Scholar 

  19. Ackman, R.G., P. Linstead, B.J. Wakefield, and B.C.L. Weedon, Tetrahedron 8:221 (1960).

    Article  CAS  Google Scholar 

  20. Gunstone, F.D., and I.A. Ismail, Chem. Phys. Lipids 1:209 (1967).

    Article  CAS  Google Scholar 

  21. Tulloch, A.P., JAOCS 41:833 (1964).

    CAS  Google Scholar 

  22. Heinz, E., A.P. Tulloch, and J.F.T. Spencer, J. Biol. Chem. 244:882 (1969).

    PubMed  CAS  Google Scholar 

  23. Craig, J.C., and E.C. Horning, J. Org. Chem. 25:2098 (1960).

    Article  Google Scholar 

  24. Djerassi, C., R.R. Engle, and A. Bowers, Ibid. 21:1547 (1956).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Prairie Regional Laboratory, National Research Council of Canada, S7N 0W9, Saskatoon, Saskatchewan

    A. P. Tulloch

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  1. A. P. Tulloch
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NRCC No. 15663.

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Tulloch, A.P. Preparation of specifically dideuterated octadecanoates and oxooctadecanoates. Lipids 12, 92–98 (1977). https://doi.org/10.1007/BF02532978

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  • DOI: https://doi.org/10.1007/BF02532978

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