Journal of Organic Chemistry p. 337 - 345 (1980)
Update date:2022-08-04
Topics:
Dias, Jerry Ray
Nassim, Bahman
The current mechanistic understanding and evidence for the decreasing preferential order (12α > 7α > 3α) of consecutive loss of three carboxylic acid or three water molecules from the molecular ion of 3α,7α,12α-tricarboxy-5β-cholanoates or 3α,7α,12α-trihydroxy-5β-cholanoates, respectively, are summarized.Additional mechanistic details for water loss have been determined with the aid of deuterium labeling.The fragmentation pathways of 3α,7α,12α-triacetoxy-5β-pregnan-20-one, a bile acid derivative, have been defined by comparison with four deuterated analogues.Evidence for the nominal loss of acetic anhydride or its equivalent from triacetate esters of cholic acid is presented.
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