| 芴甲氧羰基酪氨酸苄醚的合成研究 |
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| 引用本文： | 施志浩,魏运洋,丁亚明,杨鹏.芴甲氧羰基酪氨酸苄醚的合成研究[J].化学试剂,2006,28(4):199-201. |
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| 作者姓名： | 施志浩 魏运洋 丁亚明 杨鹏 |
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| 作者单位： | 南京理工大学,化工学院,江苏,南京,210094 |
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| 摘 要： | 研究了硫酸铜存在下溴苄与酪氨酸反应生成酪氨酸苄醚,收率45%。反应中,铜盐先与酪氨酸的羧基作用,生成4∶1的酪氨酸铜配合物,从而有效地保护了酪氨酸的羧基,使苄基化反应选择性地发生在侧链酚基氧原子上。酪氨酸苄醚与芴甲氧羰酰氯在THF中反应得标题化合物,收率98%。
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| 关 键 词： | 酪氨酸 苄醚 氨基酸配合物 内吗啡肽 |
| 文章编号： | 0258-3283（2006）04-0199-03 |
| 收稿时间： | 2005-07-11 |
| 修稿时间： | 2005-07-11 |
Studies on the synthesis of N-fluorenylmethoxycarbonyl-O-benzyl tyrosine |
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| SHI Zhi-hao,WEI Yun-yang,DING Ya-ming,YANG Peng.Studies on the synthesis of N-fluorenylmethoxycarbonyl-O-benzyl tyrosine[J].Chemical Reagents,2006,28(4):199-201. |
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| Authors: | SHI Zhi-hao WEI Yun-yang DING Ya-ming YANG Peng |
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| Affiliation: | College of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, China |
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| Abstract: | The synthesis of N-fluorenylmethoxycarbonyl-O-benzyl tyrosine was studied.Reaction of L-tyrosine with benzyl bromide in the presence of copper sulfate led to the selective benzylation of phenol group on the side chain of L-tyrosine to give H-Tyr(Bzl)-OH in 45% yield via a four coordinated copper complex intermediate.The formation of copper complex intermediate protected the carboxyl group of L-tyrosine effectively and led the benzylation take place on the side chain of L-tyrosine.H-Tyr(Bzl)-OH then reacted with fluorenylmethyl chloroformate in THF to give N-fluorenylmethoxycarbonyl-O-benzyl tyrosine in 98% yield. |
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| Keywords: | tyrosine benzyl ether amino acid complexes endomorphin |
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