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Transformed steroids

Communication 63. New reaction of 16α,17α-epoxy-16β-methylsteroids — The formation of 16α,17α-cyclosulfates

  • Organic and Biological Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The reaction of 16α,17α-oxides of 16β-methylsteroids with H2SO4 in (CH3CO)2O leads to the formation of the 16,17-cyclosulfates of 16α,17α-diols.

  2. 2.

    Replacing the 20-keto group by either the hydrazone or the acetoxy group does not change the direction of the reaction.

  3. 3.

    The discovered reaction also takes place in the case of the monocyclic ditertiary oxides.

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Literature cited

  1. A. V. Kamernitskii and A. V. Skorova, Izv. Akad. Nauk SSSR, Ser. Khim., 190 (1974).

  2. A. A. Akhrem, I. V. Vesela, and A. V. Kamernitskii, Izv. Akad. Nauk SSSR, Ser. Khim., 2552 (1971).

  3. P. D. Bragg and J. K. N. Jones, Can. J. Chem.,37, 1412 (1959).

    Google Scholar 

  4. J. Fried, E. F. Sabo, P. Grabowich, L. J. Lerner, W. B. Kessler, D. M. Brennan, and A. Borman, Chem. Ind. (London), 465 (1961).

  5. L. J. Bellamy, New Data on the Infrared Spectra of Complex Molecules [Russian translation], Mir (1971), p. 241.

  6. A. A. Akhrem, V. A. Dubrovskii, A. V. Kamernitskii, and T. F. Solov'eva, Izv. Akad. Nauk SSSR, Ser. Khim., 850 (1967).

  7. A. A. Akhrem, V. A. Doubrovsky, A. V. Kamernitzky, and A. V. Skorova, Tetrahedron,25, 4737 (1969).

    Google Scholar 

  8. A. A. Akhrem, I. V. Vesela, A. V. Kamernitskii, and E. P. Prokof'ev, Izv. Akad. Nauk SSSR, Ser. Khim., 1119 (1972).

  9. P. Crabbé, Tetrahedron,19, 51 (1963).

    Google Scholar 

  10. J. Fried, US Patent 3049540 (1962); Chem. Abstr.,58, 5763 (1963).

    Google Scholar 

  11. A. A. Akhrem, V. A. Dubrovskii, A. V. Kamernitskii, and A. M. Moiseenkov, Izv. Akad. Nauk SSSR, Ser. Khim., 109 (1967).

  12. A. Casadevall, A. Commeyras, P. Paillons, and H. Collet, Bull. Soc. Chim. France, 719 (1970).

  13. A. A. Akhrem, A. V. Kamernitskii, and A. V. Skorova, Izv. Akad. Nauk SSSR, Ser. Khim., 416 (1972).

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    A. A. Akhrem, I. V. Vesela & A. V. Kamernitskii

Authors
  1. A. A. Akhrem
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  2. I. V. Vesela
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  3. A. V. Kamernitskii
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Additional information

See [1] for Communication 62.

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 416–422, February, 1974.

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Akhrem, A.A., Vesela, I.V. & Kamernitskii, A.V. Transformed steroids. Russ Chem Bull 23, 383–388 (1974). https://doi.org/10.1007/BF00924693

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  • DOI: https://doi.org/10.1007/BF00924693

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