Potential bile acid metabolites. 24. An efficient synthesis of carboxyl-linked glucosides and their chemical properties

Takashi Iida, Ryusei Nakamori, Rie Yabuta, Satoru Yada, Yuzuru Takagi, Nariyasu Mano, Shigeo Ikegawa, Junichi Goto, Toshio Nambara

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

A facile and efficient synthesis of the carboxyl-linked glucosides of bile acids is described. Direct esterification of unprotected bile acids with 2,3,4,6-tetra-O-benzyl-D-glucopyranose in pyridine in the presence of 2-chloro-1,3,5-trinitrobenzene as a coupling agent afforded a mixture of the α- and β-anomers (ca. 1:3) of the 1-O-acyl-D-glucoside benzyl ethers of bile acids, which was separated effectively on a C18 reversed-phase chromatography column (isolated yields of α- and β-anomers are 4-9% and 12-19%, respectively). Subsequent hydrogenolysis of the α- and β-acyl glucoside benzyl ethers on a 10% Pd-C catalyst in acetic acid/methanol/EtOAc (1:2:2, by vol) at 35°C under atmospheric pressure gave the corresponding free esters in good yields (79-89%). Chemical specificities such as facile hydrolysis and transesterification of the acyl glucosides in various solvents were also discussed.

Original languageEnglish
Pages (from-to)101-110
Number of pages10
JournalLipids
Volume37
Issue number1
DOIs
Publication statusPublished - 2002

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Cell Biology

Fingerprint Dive into the research topics of 'Potential bile acid metabolites. 24. An efficient synthesis of carboxyl-linked glucosides and their chemical properties'. Together they form a unique fingerprint.

Cite this