Synthesis of new bile salt analogues, sodium 3 alpha, 7 alpha-dihydroxy-5 beta-cholane-24-sulfonate and sodium 3 alpha, 7 beta-dihydroxy-5 beta-cholane-24-sulfonate.
This report describes the chemical synthesis of two new bile salt analogues, namely sodium 3 alpha,7 alpha-dihydroxy-5 beta-cholane-24-sulfonate and sodium 3 alpha,7 beta-dihydroxy-5 beta-cholane-24-sulfonate from chenodeoxycholic acid and ursodeoxycholic acid, respectively. Each common bile acid was converted into the corresponding 5 beta-cholane-3,7,24-triol by treatment with ethyl chloroformate in the presence of triethylamine followed by sodium borohydride reduction. Reaction of the cholanetriol with p-toluenesulfonyl chloride at 4 degrees C afforded the partially tosylated product, 24-p-toluenesulfoxy-5 beta-cholane-3,7-diol, which was then treated with sodium iodide to produce 24-iodo-5 beta-cholane-3,7-diol. The 24-iodide was refluxed with sodium sulfite in aqueous ethanol to give the desired sulfonate analogue of the naturally occurring bile acid, chenodeoxycholic acid or ursodeoxycholic acid.
Kihira
K
K
Institute of Pharmaceutical Science, Hiroshima University School of Medicine, Japan.
Yoshii
M
M
Okamoto
A
A
Ikawa
S
S
Ishii
H
H
Hoshita
T
T
D001647:Bile Acids and Salts; D055598:Chemical Phenomena; D002621:Chemistry; D002635:Chenodeoxycholic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D002855:Chromatography, Thin Layer; D015394:Molecular Structure
D001647:Bile Acids and Salts; D002635:Chenodeoxycholic Acid; C065714:3,7-dihydroxycholane-24-sulfonate