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13C NMR spectra and structure of 16α, 17α-cyclohexanopregnanes with sulfur-containing substituents in rings A and B

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

Conclusions

  1. 1.

    The high-resolution13C NMR spectra were analyzed for 16α, 17α-cyclohexanopregnanes substituted in rings A and B by SR (R=Ph, CH2CH2SH) and S(O)Ph groups. These spectra were used to determine the position of the double bond (Δ4 or Δ5) and the position and orientation of the 3α-SR, 3β-SR, 5α-SR, and 3β-S(O)Ph substituents.

  2. 2.

    The α-, gb-, γ-, and δ-effects of the SR (R=Ph, CH2CH2SH) and S(O)Ph substituents on the chemical shifts of the carbon atoms of the steroid skeleton were determined and analyzed. A diastereotopic effect of the S(O)Ph group on the chemical shifts of the carbon atoms of rings A and B was discovered.

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Authors and Affiliations

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

    E. G. Cherepanova, V. S. Bogdanov, I. S. Levina & L. E. Kulikova

Authors
  1. E. G. Cherepanova
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  2. V. S. Bogdanov
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  3. I. S. Levina
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  4. L. E. Kulikova
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1046–1051, May, 1989.

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Cherepanova, E.G., Bogdanov, V.S., Levina, I.S. et al. 13C NMR spectra and structure of 16α, 17α-cyclohexanopregnanes with sulfur-containing substituents in rings A and B. Russ Chem Bull 38, 946–950 (1989). https://doi.org/10.1007/BF00955423

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  • DOI: https://doi.org/10.1007/BF00955423

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