The Structure of 16, 17β-epoxy-17α-pregn-5-en-3β-ol-20-one Monohydrate

Authors

Sergey Lindeman, Marquette UniversityFollow
A. M. Turuta, Russian Academy of SciencesFollow
Yu T. Struchkov, Russian Academy of SciencesFollow
Alexey V. Kamernitzky, Zelinsky Institute of Organic ChemistryFollow

Document Type

Article

Language

eng

Publication Date

2-1993

Publisher

Springer

Source Publication

Russian Chemical Bulletin

Source ISSN

1066-5285

Abstract

The structure of the title compound (1) has been studied by means of X-ray diffraction. The region of cycleD in epoxide1 was compared with that of the 16,17α-epoxy derivatives of progesterone and pregnenolone (studied previously) as well as with that of the respective 16,17α- and 16,17β-cyclopropano analogs. In contrast to the 16,17α-epoxy-20-oxo derivatives, in compound1 the electron conjugation of the epoxide ring with the CH₃CO group at C(17) is partly disrupted. Moreover, the steric congestion at C(17) is significantly less pronounced in 16,17β-epoxide1 than in its 16,17α-counterpart. Both of these factors, especially steric decongestion, are favorable for nucleophilic attack at C(17) in the molecule of1. The X-ray diffraction data do not contradict the previously advanced mechanism of epoxide ring opening in 16,17α- and 16,17β-epoxy-20-oxo steroids by nucleophilic reagents.

Comments

Russian Chemical Bulletin, Vol. 42, No. 2 (February 1993): 365-370. DOI.

Sergey Lindeman was affiliated with Russian Academy of Sciences at the time of publication.

Recommended Citation

Lindeman, Sergey; Turuta, A. M.; Struchkov, Yu T.; and Kamernitzky, Alexey V., "The Structure of 16, 17β-epoxy-17α-pregn-5-en-3β-ol-20-one Monohydrate" (1993). Chemistry Faculty Research and Publications. 709.
https://epublications.marquette.edu/chem_fac/709