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Transformed steroids

Communication 4. Synthesis, properties, and reactions of 3β, 16α, 17α-trihydroxypregn-5-en-20-one

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    Various ways of synthesizing 3β,16α,17α-trihydroxypregn-5-en-20-one were investigated, and some of its reactions were studied.

  2. 2.

    3β,16α,17α-Trihydroxypregn-5-en-20-one undergoes D-homo isomerization of the crystalline condition when heated below the melting point and so does not have a true melting point.

  3. 3.

    A study was made of the D-homo isomerization of 3β, 16α,17α-trihydroxypregn-5-en-20-one under acid and alkaline conditions and also over silica gel and in presence of ferric chloride.

  4. 4.

    From the products of the isomerization of 3β,16α,17α-trihydroxypregn-5-en-20-one the previously undescribed 3β,16α17α-trihydroxy-17β-methyl-D-homoandrost-5-en-17a-one was isolated.

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Literature cited

  1. K. Heusler and A. Wettstein, Chem. Ber.87, 1301 (1954).

    Google Scholar 

  2. H. Her. Inhoffen, F. Blomeyer, and K. Brückner, Chem. Ber.87, 593 (1954).

    Google Scholar 

  3. G. Cooley, B. Ellis, F. Hartley, and V. Petrow, J. Chem. Soc. 1955, 4377.

  4. J. Romo, Romo de Vivar, J. Organ. Chem.21, 902 (1956).

    Google Scholar 

  5. G. Cooley, B. Ellis, F. Hartley, and V. Petrow, J. Chem. Soc. 1955, 4373.

  6. B. Ellis, S. P. Hall, V. Petrow, S. Waddington-Feather, J. Chem. Soc. 1961, 4111.

  7. F. B. Colton, U. S. Pat. 2727909 (1955).

  8. S. Bernstein and R. Little, J. Amer. Chem. Soc.82, 1235 (1960).

    Google Scholar 

  9. S. Bernstein, J. Brown, L. Feldman, and N. E. Rigler, J. Amer. Chem. Soc.81, 4956 (1959).

    Google Scholar 

  10. J. S. Mills, A. Bowers, Carl Djerassi, and H. J. Ringold, J. Amer. Chem. Soc.82, 3399 (1960).

    Google Scholar 

  11. M. Heller, S. Stolar, and S. Bernstein, J. Organ. Chem.26, 5036 (1961).

    Google Scholar 

  12. S. Bernstein, R. Lehnard, W. Allen, M. Heller, R. Littel, S. Stolar, L. Feldman, and R. Blank, J. Amer. Chem. Soc.81, 1689 (1959).

    Google Scholar 

  13. N. L. Wendler, D. Taub, S. Dobriner, and D. K. Fukushima, J. Amer. Chem. Soc.78, 5027 (1956).

    Google Scholar 

  14. N. L. Wendler, D. Taub, and R. W. Walker, Tetrahedron11, 163 (1960).

    Google Scholar 

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This article is published in accordance with a resolution of the Conference of Chief Editors of Journals of the Academy of Sciences of the USSR, July 12, 1962, as a dissertation paper by V. A. Dubvorskii.

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Dubrovskii, V.A., Akhrem, A.A. & Kamernitskii, A.V. Transformed steroids. Russ Chem Bull 13, 87–93 (1964). https://doi.org/10.1007/BF01179573

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  • DOI: https://doi.org/10.1007/BF01179573

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