Advertisement

Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Transformed steroids Communication 38. Stereochemical and structural direction of the addition of thioacetic acid to 16α,17α-epoxy-Δ5-pregnen-3β-ol-20-one 3-acetate

  • 22 Accesses

Conclusions

  1. 1.

    A study was made of the homolytic and acid-catalyzed addition of thioacetic acid to 16α,17α-epoxy-Δ5-pregnen-3β-o1-20-one 3-acetate.

  2. 2.

    In both cases the reaction goes in a structurally selective manner that is contrary to the Markovnikov rule, but not stereospecifically, with the formation of the 3,6-diacetates of 6ξ-thiol-5α-pregnan-3β-o1-20-one epimeric at C6.

  3. 3.

    The structure and stereochemistry of the obtained thioacetates were established by physical and chemical methods.

This is a preview of subscription content, log in to check access.

Literature cited

  1. 1.

    M. Tomoeda, M. Inuzuka, and T. Furuta, Tetrahedron Lett., 1233 (1964).

  2. 2.

    C. W. Shoppe, M. Akhtar, and R. Lack, J. Chem. Soc., 877 (1964).

  3. 3.

    A. A. Akhrem and A. I. Kuznetsova, Izv. Akad. Nauk SSSR, Ser. Khim., 405 (1969).

  4. 4.

    K. Tori, T. Koteno, and T. Nakagawa, J. Org. Chem.,29, 1136 (1964).

  5. 5.

    L. F. Fieser and M. Fieser, Steroids [Russian translation], Mir (1964), p. 187.

  6. 6.

    P. Crabbe, M. Perez, and G. Vera, Can. J. Chem.,41, 156 (1963).

  7. 7.

    A. A. Akhrem, A. M. Turuta, and Z. I. Istomina, Izv. Akad. Nauk SSSR, Ser. Khim., 2646 (1970).

Download references

Author information

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2558–2561, November, 1971.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Akhrem, A.A., Turuta, A.M. & Prokof'ev, E.P. Transformed steroids Communication 38. Stereochemical and structural direction of the addition of thioacetic acid to 16α,17α-epoxy-Δ5-pregnen-3β-ol-20-one 3-acetate. Russ Chem Bull 20, 2422–2425 (1971). https://doi.org/10.1007/BF00854326

Download citation

Keywords

  • Steroid
  • Chemical Method
  • Structural Direction
  • Selective Manner
  • Thioacetates