Potential bile acid metabolites. 24. An efficient synthesis of carboxyl-linked glucosides and their chemical properties |
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Authors: | Takashi Iida Ryusei Nakamori Rie Yabuta Satoru Yada Yuzuru Takagi Nariyasu Mano Shigeo Ikegawa Junichi Goto Toshio Nambara |
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Affiliation: | (1) Department of Chemistry, College of Humanities & Sciences, Nihon University, Sakurajousui, Setagaya, 156-8550 Tokyo, Japan;(2) Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, 981-8578 Sendai, Japan;(3) Hoshi University, Shinagawa, Ebara, 147-8501 Tokyo, Japan |
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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 reversedphase 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. |
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