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Mass spectrometry of steroid systems

XI. Determination of the configuration of steroid alcohols

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Chemistry of Natural Compounds Aims and scope

Summary

1. The mass spectra of epimeric tertiary alcohols of the D-homoestrane series and the acetates and 17a-trideuteromethyl analogs corresponding to them have been studied. A new approach to the determination of the configuration of tertiary steroid alcohols has been proposed in which the trideuteromethyl analogs of the epimeric alcohols are subjected to mass-spectrometric analysis. The presence in the mass spectrum of an epimer of a doublet of peaks M-H2O and M-DOH indicates the a-alkyl-e-OH configuration, while the presence in the spectrum of an intense M-H2O peak shows the presence of an axial OH group.

2. The mass spectra of the epimeric secondary alcohols of the pregnane series taken with the use of a system of introducing the sample into the ion source has been investigated. It has been shown that the mass spectra of alcohols containing an a-OH group in rings C and D differ markedly from the spectra of the e-OH epimers with respect to the ratio of the intensities of the peaks M-H2O and M+.

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Authors and Affiliations

  1. Institute of the Chemistry of Natural Compounds, AS USSR, USSR

    N. S. Vul'fson, V. I. Zaretskii & V. G. Zaikin

Authors
  1. N. S. Vul'fson
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  2. V. I. Zaretskii
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  3. V. G. Zaikin
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Additional information

Khimiya Prirodnykh Soedinenii, Vol. 3, No. 6, pp. 369–382, 1967

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Vul'fson, N.S., Zaretskii, V.I. & Zaikin, V.G. Mass spectrometry of steroid systems. Chem Nat Compd 3, 312–319 (1967). https://doi.org/10.1007/BF00573047

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  • DOI: https://doi.org/10.1007/BF00573047

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