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Potential intermediates in catecholestrogen biosynthesis: Characterization of a dienol epoxide derivative and related compounds via silylation reactions and gas chromatographic/mass spectrometric analysis
Author(s) -
AbdelBaky Samy,
Le Quesne Philip W.,
Schwarz Edward,
Vouros Paul
Publication year - 1985
Publication title -
biomedical mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0306-042X
DOI - 10.1002/bms.1200121202
Subject(s) - bstfa , epoxide , silylation , trimethylsilyl , chemistry , derivative (finance) , yield (engineering) , organic chemistry , enone , reagent , chromatography , catalysis , materials science , financial economics , economics , metallurgy
During 1 H‐NMR and gas chromatographic/mass spectrometric analytical investigations of the enone epoxides 2a‐5, which are of interest as tautomers of dienol epoxides implicated in the biosynthesis of catecholestrogens, silylation reactions were observed to yield a derivative 21 of one of the putative dienol epoxide intermediates. The effect of the silylating reagents bis(trimethylsilyl)trifluoroacetamide (BSTFA) and the trimethylsilimidazole (TSIM) on a variety of steroidal ketones, ketols, enones and enone epoxides is discussed and the reaction pathways are compared.