Synthesis of ester-linked lithocholic acid dimers

Alan Turner, L. Nahar

Research output: Contribution to journalArticle

25 Citations (Scopus)

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 languageEnglish
Pages (from-to)1157-1161
Number of pages4
JournalSteroids
Volume68
DOIs
Publication statusPublished - 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 journalArticle

Turner, Alan ; Nahar, L. / Synthesis of ester-linked lithocholic acid dimers. In: Steroids. 2003 ; Vol. 68. pp. 1157-1161.
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title = "Synthesis of ester-linked lithocholic acid dimers",
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.",
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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 -