Synthesis of 3α, 7α, 14α-Trihydroxy-5β-cholan-24-oic Acid : A Potential Primary Bile Acid in Vertebrates
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概要
- 論文の詳細を見る
A method for the synthesis of 3α,7α,14α-trihydroxy-5β-cholan-24-oic acid which is a possible candidate of bile acid metabolite in vertebrates was developed. The principal reactions involved were 1) stereoselective remote-hydroxylation of methyl ursodeoxycholate diacetate with dimethyldioxirane, 2) site-selective protection at C-3 by tert-butyldimethylsilylation of the resulting 3α,7α,14α-trihydroxy ester, 3) oxidation of the diol with pyridinium dichromate adsorbed on activated alumina, 4) stereoselective reduction of the 7-ketone with zinc borohydride, and 5) cleavage of the protecting group at C-3 withp-toluenesulfonic acid. A facile elimination of the 14α-hydroxy group under an acidic or neutral condition is also described. The synthetic reference compound is now available for comparison with unidentified biliary bile acids detected in vertebrate bile.
- 社団法人日本薬学会の論文
- 2004-03-01
著者
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Mano Nariyasu
Dep. Of Pharmaceutical Sciences Tohoku Univ. Hospital
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Mano Nariyasu
東北大学 薬研究
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Mano N
Tsukuba Research Laboratories Eisai Co. Ltd.
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Mano Nariyasu
Graduate School Of Pharmaceutical Sciences Tohoku University
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IIDA Takashi
Departments of Transplantation; School of Medicine, Tokai University
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Kakiyama Genta
Department of Chemistry, College of Humanities & Sciences, Nihon University
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GOTO Junichi
Graduate School of Pharmaceutical Science, Tohoku University
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Goto J
Tohoku Univ. Sendai Jpn
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Goto J
The Ion Engineering Research Institute Corporation
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Iida Takashi
Dep. Of Chemistry Coll. Of Humanities & Sciences Nihon Univ.
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Iida Takashi
Department Of Dermatology Nara Medical University
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Mano N
Dep. Of Pharmaceutical Sciences Tohoku Univ. Hospital
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Kakiyama Genta
Dep. Of Chemistry Coll. Of Humanities & Sciences Nihon Univ.
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GOTO Takaaki
Graduate School of Pharmaceutical Sciences, Tohoku University
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NAMBARA Toshio
Graduate School of Pharmaceutical Sciences, Tohoku University
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Goto T
Graduate School Of Pharmaceutical Sciences Tohoku University
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Goto Takaaki
Department Of Electric Engineering Tokyo University Of Agriculture And Technology
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Goto J
Division Of Clinical Pharmacy Graduate School Of Pharmaceutical Sciences Tohoku University
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後藤 俊夫
名大農
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Mano Nariyasu
Analytical Chemistry And Pharmaceutical Research Section Tsukuba Research Laboratories Eisai Co. Ltd
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Nambara T
Tohoku Univ. Sendai Jpn
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Nambara T
Graduate School Of Pharmaceutical Sciences Tohoku University
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後藤 俊夫
Imram Tohoku University
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Goto Junichi
Graduate School Of Pharmaceutical Science Tohoku University
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Iida Takashi
Departmenr Of Neuropathology Neurological Institute Graduate School Of Medical Sciences Kyushu Unive
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Goto Junichi
Department of Pharmaceutical Sciences, Tohoku University Hospital
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後藤 俊夫
Graduate School of Pharmaceutical Sciences, Tohoku University
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