Abstract
Four lithocholic acid dimers were synthesised via esterification. The ester-linked dimer, 3-oxo-5beta-cholan-24-oic acid (cholan-24-oic acid methyl ester)-3-yl ester, (3alpha,5beta), was obtained by condensation of methyl lithocholate with 3-oxo-5beta-cholan-24-oic acid. Borohydride reduction of this ester-linked dimer gave 3alpha-hydroxy-5beta-cholan-24-oic acid (cholan-24-oic acid methyl ester)-3-yl ester, (3alpha,5beta), which was acetylated to 3alpha-acetoxy-5beta-cholan-24-oic acid (cholan-24-oic acid methyl ester)-3-yl ester, (3alpha,5beta). Reaction of methyl lithocholate with oxalyl chloride yielded the oxalate dimer, bis(5beta-cholan-24-oic acid methyl ester)-3alpha-yl oxalate. (C) 2003 Elsevier Inc. All rights reserved.
| Original language | English |
|---|---|
| Pages (from-to) | 1157-1161 |
| Number of pages | 4 |
| Journal | Steroids |
| Volume | 68 |
| DOIs | |
| Publication status | Published - 2003 |
Keywords
- lithocholic acid
- steroid dimers
- esterification
- hydrolysis
- C-13 NMR
- BILE-ACIDS
- STEROIDS
- DERIVATIVES
- BINDING
- BIS
Cite this
Turner, A., & Nahar, L. (2003). Synthesis of ester-linked lithocholic acid dimers. Steroids, 68, 1157-1161. https://doi.org/10.1016/j.steroids.2003.08.015