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A comparison of the mass-spectrometric properties of compounds of the pregnane series with the properties of substances similar to cardenolides

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Summary

1. The mass spectra of several intermediates in the synthesis of uzarigenin from 5α-pregn-16-enolone have been characterized. Their general features and the differences between the spectra of 14α-H and 14β-OH compounds have been discussed.

2. It has been established that all the main processes of the decomposition of the molecular ions of the compounds studied take place close to ring D, and the contribution of ring A is small. The sequences of ejection of the 3β and 20α substituents and also the characteristics of their fragmentation in dependence on their volume have been investigated.

3. Schemes are proposed which explain the fragmentation pathways of 14β, 15β-epoxy compounds.

4. It has been shown that the introduction of a double bond into the 20(22) position of 14β-hydroxy steroids leads to the appearance in the mass spectra of fragments due to the decomposition that is typical for the cardenolides.

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Authors
  1. Ya. V. Rashkes
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  2. M. B. Gorovits
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  3. F. S. Khristulas
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  4. N. K. Abubakirov
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Additional information

Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 309–317, May–June, 1972.

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Rashkes, Y.V., Gorovits, M.B., Khristulas, F.S. et al. A comparison of the mass-spectrometric properties of compounds of the pregnane series with the properties of substances similar to cardenolides. Chem Nat Compd 8, 306–312 (1972). https://doi.org/10.1007/BF00563736

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  • DOI: https://doi.org/10.1007/BF00563736

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