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  • 标题:An Efficient Synthesis of N-tert-Butoxycarbonyl-O-cyclohexyl-L-tyrosine
  • 本地全文:下载
  • 作者:Yasuhiro NISHIYAMA ; Sou ISHIZUKA ; Suguru SHIKAMA
  • 期刊名称:Chemical and Pharmaceutical Bulletin
  • 印刷版ISSN:0009-2363
  • 电子版ISSN:1347-5223
  • 出版年度:2001
  • 卷号:49
  • 期号:2
  • 页码:233-235
  • DOI:10.1248/cpb.49.233
  • 出版社:The Pharmaceutical Society of Japan
  • 摘要:

    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 PtO2 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.

  • 关键词:cyclohexyl; tyrosine; cyclohex-2-enyl; protecting group; hydroxy
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