Potential bile acid metabolites. 16. Synthesis of stereoisomeric 3 alpha,6,7,12 alpha-tetrahydroxy-5 beta-cholanoic acids.
New synthetic routes to the four possible stereoisomeric 3 alpha,6,7,12 alpha-tetrahydroxy-5 beta-cholanoic acids (and their methyl esters), one of which (3 alpha,6 alpha 7 beta,12 alpha) is new, and some related compounds are described. In addition, the 5 alpha-epimer of the new acid was obtained. The final products were obtained in high purity for use as reference compounds in the analysis of bile acids in human biologic samples. The results of analysis of the prepared stereoisomers by proton and carbon 13 nuclear magnetic resonance spectroscopies are briefly discussed along with the thin-layer and gas-liquid chromatographic properties.
Iida
T
T
College of Engineering, Nihon University, Fukushima-ken, Japan.
Komatsubara
I
I
Yoda
S
S
Goto
J
J
Nambara
T
T
Chang
F C
FC
D001647:Bile Acids and Salts / Q000378:metabolism*; D055598:Chemical Phenomena; D002621:Chemistry; D002793:Cholic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002849:Chromatography, Gas; D002855:Chromatography, Thin Layer; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
D001647:Bile Acids and Salts; D002793:Cholic Acids