Transformed steroids

Communication 41. Reaction of 3-acetate of 16α, 17α-epoxy-δ5-pregnen-3/gb-ol-20-one with thiolacetic acid and synthesis of δ5-pregnene-3β,16/gb, 17α-triol-20-one 3-acetate, 16-thionoacetate
  • A. A. Akhrem
  • A. M. Turuta
  • E. P. Prokof'ev
Organic and Biological Chemistry


  1. 1.

    A method was developed for opening the oxide ring of the 3-acetate of 16α, 17α-epoxy-Δ5-pregnen-3β-ol-20-one with thiolacetic acid under ionic conditions.

  2. 2.

    The reaction proceeds with a predominant cleavage of the C16-O bond of the oxide ring and attack of the C16-center by the thiolacetic acid in the thiono form, with the formation of the 3-acetate, 16-thionoacetate of Δ5-pregnene-3β, 16β,17α-triol-20-one, the structure of which was assigned on the basis of the sum of the chemical and physicochemical methods.

  3. 3.

    A small amount (~ 6%) of the isomeric product of opening the ring is formed, which apparently arises as the result of the cleavage of the C17-O bond of the starting oxide by the thiol form of thiolacetic acid.



Oxide Steroid Thiol Ionic Condition Physicochemical Method 
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Copyright information

© Consultants Bureau 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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