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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

  • A. A. Akhrem
  • A. M. Turuta
  • E. P. Prokof'ev
Organic and Biological Chemistry
  • 21 Downloads

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.

     

Keywords

Steroid Chemical Method Structural Direction Selective Manner Thioacetates 
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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Literature cited

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Copyright information

© Consultants Bureau, a division of Plenum Publishing Corporation 1972

Authors and Affiliations

  • A. A. Akhrem
    • 1
  • A. M. Turuta
    • 1
  • E. P. Prokof'ev
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRUSSR

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