Conclusions
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1.
We deciphered the3C spectra of 19 steroids with additional tetrahydropyran and tetrahydrofuran rings and modified in the A and B rings.
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2.
The chemical shifts and spin-spin coupling constants for13C-1H are characteristic for the two conformations of the tetrahydropyran E ring, “chair” and “boat.”
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3.
We determined the orientation of the substituents at C20 and confirmed the orientation for substituents at C3, C5, and C6.
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4.
We carried out an analysis of theα-,β-,γ-, andδ-effects for substituents in the tetrahydropyran ring and the A and B rings. We have shown that acetylation of the 20-OH group enhances theα-effect; theβ-effects decrease in the order O > OH > OAc.
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5.
The dependence of the spin-spin coupling constants for13C-1H on the nature of the substituent may be used to identify signals of the ring carbon atoms, along with their chemical shifts.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No, 3, pp. 549–560 March, 1983.
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Bogdanov, V.S., Cherepanova, E.G., Reshetova, I.G. et al. 13C,1H NMR spectra and the structure of steroids containing a perhydropyran or perhydrofuran E ring and modification in the A and B rings. Russ Chem Bull 32, 492–501 (1983). https://doi.org/10.1007/BF00953082
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DOI: https://doi.org/10.1007/BF00953082