The structure of 16, 17β-epoxy-17α-pregn-5-en-3β-ol-20-one monohydrate.
In: Russian Chemical Bulletin, Jg. 42 (1993-02-01), Heft 2, S. 365-370
Online
academicJournal
Zugriff:
The structure of the title compound ( 1) has been studied by means of X-ray diffraction. The region of cycle D in epoxide 1 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 compound 1 the electron conjugation of the epoxide ring with the CHCO group at C(17) is partly disrupted. Moreover, the steric congestion at C(17) is significantly less pronounced in 16,17β-epoxide 1 than in its 16,17α-counterpart. Both of these factors, especially steric decongestion, are favorable for nucleophilic attack at C(17) in the molecule of 1. 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. [ABSTRACT FROM AUTHOR]
Copyright of Russian Chemical Bulletin is the property of Springer Nature and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
Titel: |
The structure of 16, 17β-epoxy-17α-pregn-5-en-3β-ol-20-one monohydrate.
|
---|---|
Autor/in / Beteiligte Person: | Lindeman, S. ; Turuta, A. ; Struchkov, Yu. ; Kamernitskii, A. |
Link: | |
Zeitschrift: | Russian Chemical Bulletin, Jg. 42 (1993-02-01), Heft 2, S. 365-370 |
Veröffentlichung: | 1993 |
Medientyp: | academicJournal |
ISSN: | 1066-5285 (print) |
DOI: | 10.1007/BF00697098 |
Sonstiges: |
|