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

研究成果: Article査読

15 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)101-110
ページ数10
ジャーナルLipids
37
1
DOI
出版ステータスPublished - 2002

ASJC Scopus subject areas

  • 生化学
  • 有機化学
  • 細胞生物学

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