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
Synthesis of ester-linked lithocholic acid dimers. / Turner, Alan; Nahar, L.
In: Steroids, Vol. 68, 2003, p. 1157-1161.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis of ester-linked lithocholic acid dimers
AU - Turner, Alan
AU - Nahar, L.
PY - 2003
Y1 - 2003
N2 - 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.
AB - 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.
KW - lithocholic acid
KW - steroid dimers
KW - esterification
KW - hydrolysis
KW - C-13 NMR
KW - BILE-ACIDS
KW - STEROIDS
KW - DERIVATIVES
KW - BINDING
KW - BIS
U2 - 10.1016/j.steroids.2003.08.015
DO - 10.1016/j.steroids.2003.08.015
M3 - Article
VL - 68
SP - 1157
EP - 1161
JO - Steroids
JF - Steroids
SN - 0039-128X
ER -