Bile acids. LXXXI. Synthesis and structural assignment of E/Z isomers of substituted methyl hydroxy-5 beta-cholest-24-en-26-oates.
Syntheses of the E and Z isomers of methyl 3 alpha-,3 alpha,7 alpha-,3 alpha,12 alpha-, and 3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholest-24-en-26-oates are reported. Mass spectral studies show fragmentation patterns in support of assignment as the E or Z isomers, especially in differences in loss of the side chain. Chromatographic procedures, primarily gas chromatography and high-performance liquid chromatography, support these assignments. The E isomer predominates in either of two methods of synthesis.
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Edward A. Doisy Department of Biochemistry and Molecular Biology, St. Louis University School of Medicine, Missouri 63104.
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Elliott
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D001647:Bile Acids and Salts / Q000737:chemistry*; D002757:Cholanes / Q000737:chemistry; D002782:Cholestenes / Q000138:chemical synthesis; D013058:Mass Spectrometry; D015394:Molecular Structure; D013237:Stereoisomerism
D001647:Bile Acids and Salts; D002757:Cholanes; D002782:Cholestenes; C073869:methyl-3,7,12-trihydroxycholest-24-ene-26-oate; C073868:3,7,12-triformoxycholan-24-al