Chemistry of Novel Compounds Possessing Multifunctional Carbon Atoms. X. Synthetic Studies of Efficient and Practical Chiral Derivatizing Agents Based on the α-Cyano-α-fluorophenylacetic Acid Structure
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概要
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In order to develop efficient chiral derivatizing agents (CDAs) which can be obtained readily in optically active form, synthetic studies of α-cyano-α-fluorophenylacetic acid (CFPA) analogs, 3a-e and CFNA (14a), were made. Carboxylation of 6a-e obtained from 4a-e gave 3a-e in low yield. Alternatively, benzyl cyanides 5b-e were converted successfully to the esters 7b-e, 8b-e, and 9b-e, which were fluorinated with FClO_3 to produce the fluoro esters 10b-e, 11b-e, and 12b-d, in good yields. However, the attempted ester cleavage of these compounds did not give 3b-e. Carboxyl group introduction into 5e afforded 13,and fluorination with either F_2 or FClO_3 gave complex mixtures.Carboxylation of the naphthyl analog 16 obtained from 15 did not give 14a. However, fluorination of 18 derived from 17 proceeded readily to give 19,which was hydrolyzed to produce 14a. Optically active (-)-14a was obtained through enzymatic hydrolysis. The racemic acid 14a was condensed with three representative chiral nucleophiles to give 14b-d. From the ^1H- and ^<19>F-NMR spectra of these derivatives, it was concluded that CFNA (14a) is potentially a much better CDA than the well known α-methoxy-α-(trifluoromethyl)phenylacetic acid (MTPA).
- 社団法人日本薬学会の論文
- 1995-10-15
著者
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小泉 徹
富山医科薬科大学薬学部薬化学
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小泉 徹
Faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University
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甲 国信
Faculty Of Science Tohoku University
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竹内 義雄
富山大院医薬
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竹内 義雄
Faculty Of Pharmaceutical Sciences University Of Tokyo
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Koizumi T
Faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University
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黒瀬 規之
富山医科薬科大学薬学部薬化学
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岩下 英史
Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University
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山田 康司
Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University
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五太子 まゆみ
Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University
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黒瀬 規之
Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University
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米谷 正
Department of Chemical and Biochemical Engineering, Toyama National College of Technology
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五太子 まゆみ
Faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University
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山田 康司
Faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University
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Yamada Kohji
Faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University
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米谷 正
Department Of Chemical And Biochemical Engineering Toyama National College Of Technology
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小泉 徹
Department Of Synthetic Organic Chemistry:faculty Of Pharmaceutical Sciences Toyama Medical And Phar
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岩下 英史
Faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University
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Koizumi Toru
Faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University
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