The characteristic mass spectral fragmentation patterns of the basic structure of the steroidal sapogenin, (2SR)-Sa-spirostan, have been elucidated through the preparation of analogs with deuterium labels at positions 1 1 , 12, 14, 15, 16, 17,20,21,23,24,25,26 and 27. In addition, the effects of a change of stereochemistry at positions 14 and 20, of the introduction of oxygencontaining functionalities mostly in ring F, and of the incorporation of olefinic unsaturation have been determined through synthesis of many examples.
The possibility of a mass spectrometric counterpart to the cyclobutanol formation which is encountered in the photolysis of carbonyl compounds has been investigated by preparing 5,5,5-[2H,]-2-methylpentanal (11) and 6,6,6-[2H,]-3-methyIhexan-2-one (111) and examining their mass spectra at high and low voltage.
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