13C-NMR and mass spectral data of steroids with a 17,17-dialkyl-18-nor-13(14)-ene substructure

13C-NMR and mass spectral data of steroids with a 17,17-dialkyl-18-nor-13(14)-ene substructure

We present carbon-13 nuclear magnetic resonance (13C-NMR) and mass spectral data for several androstanes and estranes having a 17,17-dialkyl-18-nor-13(14)-ene substructure. These compounds are formed by a Wagner-Meerwein rearrangement of steroids bearing a tertiary 17-hydroxy group during the deriva...

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Bibliographic Details
Main Authors: V I De Brabandere, L M Thienpont, D Stöckl, A P De Leenheer
Format: Article
Language:English
Published: Elsevier 1997-04-01
Series:Journal of Lipid Research
Online Access:http://www.sciencedirect.com/science/article/pii/S0022227520372448
Description
Summary:We present carbon-13 nuclear magnetic resonance (13C-NMR) and mass spectral data for several androstanes and estranes having a 17,17-dialkyl-18-nor-13(14)-ene substructure. These compounds are formed by a Wagner-Meerwein rearrangement of steroids bearing a tertiary 17-hydroxy group during the derivatization reaction with heptafluorobutyric anhydride. The 13C-NMR assignments are compared with those of natural products having a similar substructure. The mass spectra show characteristic fragment ions for which a fragmentation mechanism is proposed.
ISSN:0022-2275

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