芴甲氧羰基酪氨酸苄醚的合成研究

Studies on the synthesis of N-fluorenylmethoxycarbonyl-O-benzyl tyrosine

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%。

The synthesis of N-fluorenylmethoxyearbonyl-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.