An Efficient Synthesis of N-tert-Butoxycarbonyl-O-cyclohexyl-L-tyrosine
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概要
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A facile and efficient synthesis of N-tert-butoxycarbonyl-O-cyclohexyl-L-tyrosine[Boc-Tyr(Chx)-OH]is described. Boc-Tyr-OH was treated with NaH in dimethylformamide and then with 3-bromocyclohexene to give N-Boc-O-(cyclohex-2-enyl)-L-tyrosine[Boc-Tyr(Che)-OH]in 70% yield. Hydrogenation of Boc-Tyr(Che)-OH over PtO_2 afforded Boc-Tyr(Chx)-OH in almost quantitative yield. The highest yield was achieved when a side product in the synthesis of Boc-Tyr-OH, Boc-Tyr(Boc)-OH, was not removed, because it was also converted to Boc-Tyr(Che)-OH without any additional manipulations. The new synthetic method described here is convenient for practical use, and would facilitate the widespread use of the Chx group for the hydroxy-protection of Tyr.
- 公益社団法人日本薬学会の論文
- 2001-02-01
著者
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Nishiyama Yasuhiro
Department of Cardiology, Kurume University Medical Center
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KURITA Keisuke
Department of Industrial Chemistry, Faculty of Engineering, Seikei University
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Saito S
Department Of Pharmaceutical Molecular Biology Graduate School Of Pharmaceutical Sciences Tohoku Uni
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ISHIZUKA Sou
Department of Industrial Chemistry, Faculty of Engineering, Seikei University
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SHIKAMA Suguru
Department of Industrial Chemistry, Faculty of Engineering, Seikei University
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Ishizuka Sou
Department Of Industrial Chemistry Faculty Of Engineering Seikei University
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Kurita K
Department Of Applied Chemistry Faculty Of Engineering Seikei University
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Kurita Keisuke
Department Of Applied Chemistry Faculty Of Engineering Seikei University
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Kurita Keisuke
Department Of Materials And Life Science Faculty Of Science And Technology Seikei University
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Nishiyama Y
Department Of Pathology And Laboratory Medicine The University Of Texas-houston Medical School
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Nishiyama Yasuhiro
Department Of Applied Chemistry Osaka University
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Nishiyama Y
Department Of Natural Medicinal Chemistry Kobe Pharmaceutical University
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