CAS: 19391-35-6; (S)-Benzyl 2-((Tert-Butoxycarbonyl)Amino)-3-(4-Hydroxyphenyl)Propanoate

该化合物是氨基酸乙酰乙酰酯的一种衍生物,其特点是存在一种乙型丁基氧基碳酸(Boc)保护组和苯基乙酰基酸酯,该化合物通常用于peptide合成,作为一种受保护的乙酸合成形式,允许有选择地作出反应,同时又不干扰氨基酸的功能组.Boc组为氨基化合物提供了稳定性和保护,而苯基酯保护了碳本酸组.Bec-Tyr-Obzl通常是白色的对非白基固的,在二氯甲烷和二甲基丙基胺酯等有机溶剂中是溶性,但较少溶于水中.在标准实验室条件下,该化合物在有机合成和丙酸化学中是一种宝贵的中间体.该化合物可以在酸性条件下进行保护,从而产生自由的硫酸,然后可以将之纳入全氟基酸基酸的化合物,作为重要的生化材料的合成材料.

结构式图片

相似化合物

5513-40-6 42406-77-9 3978-80-1

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CAS号3978-80-1 N-B°C-L-酪氨酸 | CAS号100-39-0 溴化苄 | CAS号42406-77-9 H-酪氨酸-OBzl | CAS号41840-28-2 S-B°C-2-巯基-4,6-二甲基嘧啶 | CAS号24424-99-5 二碳酸二叔丁酯 | CAS号60-18-4 L-酪氨酸 | CAS号3978-80-1 N-B°C-L-酪氨酸

合成工艺路线路线简述

    L-酪氨酸置于碳酸氢钠,Potassium Carbonate体系中,用 1,4-二氧六环,水,N,N-二甲基甲酰胺 用作溶剂,化学反应生成丁氧羰基-酪氨酸-苄氧基酯
    参考文献:由含修饰酪氨酸的肽光化学形成醌甲基化物†
    标题:由含修饰酪氨酸的肽光化学形成醌甲基化物†
    摘要:我们已经证明,可以在肽结构中引入甲基苯醌(qm)前体,并用作肽修饰的光开关单元.在曼尼希反应中由受保护的酪氨酸制备qm前体1,并进一步用作肽合成的基础.此外,可以通过曼尼希反应将含有酪氨酸的肽转化成可光活化的qm前体,该反应可以提供单取代的衍生物2或双取代的衍生物3.通过在ch 3中的制备性辐射研究了修饰的酪氨酸1和二肽2和3的光化学反应性发生光脱氨基和光甲烷分解的oh.在肽结合qm前体经历photomethanolysis与量子效率φ-[r = 0.1-0.2,其中所述肽主链,不影响其光化学反应性.从二肽形成qms通过激光闪光光解检测(λ最大~400纳米,τ= 100 μs-20 Ms),并研究了它们与亲核试剂的反应性.因此,源自酪氨酸的qm前体可以是肽骨架的一部分,在电子激发后可以转化为qm,从而导致肽与不同试剂的反应.该原理证明显示了光化学引发肽修饰和与其他分子相互作用的能力,可
    Doi:10.1039/c6Ob02191C

    海关参考信息

    专利信息


    专利号:EP-1764352-A1
    优先权日:2005-08-17
    标题:A conventional method for the preparation of new precursor of no-carrier-adde O-(2-[18F]fluoroethyl)-L-tyrosine
    发明人:WANG HSIN ER; WU SHIH YAN; LIN WUU JYH; LO AI REN; CHEN JENN TZONG; LI MING HSIN
    权利人:INST NUCLEAR ENERGY RES
    摘要:This is a new precursor and new method for the synthesis of no-carrier-added O -(2-[ 18 F]fluoroethyl)-L-Tyrosine which has been proved a suitable PET (position emission tomography) probe for tumor diagnosis imaging. n The preparation of the title compound starts from precursors with the chemical structures as in Formula 1, wherein R 1 is a protective group for the carboxyl functional group, R 2 is a protective group for the amino group, and R 3 acts as a leaving group. R 1 represents an arylalkyl group, R 2 represents a carboxyl group, and R 3 represents a p -tosyloxy, methane sulfonyloxy or trifluoromethane sulfonyloxy or bromine. The invention includes a method for the syntheses of new precursors with the chemical structures as in Formula 1.n nFormula 1 : Synthesis precursors for O -(2-[ 18 F]fluoroethyl)-L-Tyrosine.

    专利号:US-7138540-B1
    优先权日:2005-09-06
    标 题:Convenient method for the preparation of new precursor of no-carrier-added O-(2-[18F]fluoroethyl)-L-Tyrosine)
    发明人:CHEN JENN TZONG; LIN WUU JYH; LO AI REN; LEE MING HSIN; WANG HSIN ER; WU SHIH YAN
    权利人:INST NUCLEAR ENERGY RES
    摘要:This is a new precursor and new method for the synthesis of no-carrier-added O-(2-[ 18 F]fluoroethyl)-L-Tyrosine which has been proved a suitable PET (position emission tomography) probe for tumor diagnosis imaging, the preparation of the title compound starts from precursors with the chemical structures as in Formula 1, wherein R 1 is a protective group for the carboxyl functional group, R 2 is a protective group for the amino group, and R 3 acts as a leaving group. R 1 represents an arylalkyl group, R 2 represents a carboxyl group, and R 3 represents a p-tosyloxy, methane sulfonyloxy or trifluoromethane sulfonyloxy or bromine, the invention includes a method for the syntheses of new precursors with the chemical structures as in Formula 1.

    专利号:US-7132563-B1
    优先权日:2005-09-06
    标 题 :Convenient method for the preparation of no-carrier-added O-(2-[18F]fluoroethyl)-L-tyrosine)
    发明人:CHEN JENN TZONG; LIN WUU JYH; LO AI REN; LEE MING HSIN; WANG HSIN ER; WU SHIH YAN; CHANG MAO HSIUNG
    权利人:INST NUCLEAR ENERGY RES
    摘要:This is a novel method for production of no-carrier-added O-(2-[ 18 F]fluoroethyl)-L-Tyrosine, which has been proved a suitable PET (position emission tomography) probe for tumor diagnosis imaging, and the preparation of the title compound starts from precursors with the chemical structures as in Formula 1, wherein R 1 is a protective group for the carboxyl functional group, R 2 is a protective group for the amino group, and R 3 acts as a leaving group, R 1 represents an arylalkyl group, R 2 represents a carboxyl group, and R 3 represents a p-tosyloxy, methane sulfonyloxy or trifluoromethane sulfonyloxy or bromine, and the final purification of the product is using a separation column, which is very convenient for automated synthesis, and the invention uses the precursor with the chemical structures as in Formula 1.
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    主要参考文献

    [参考文献]: Luckose F, Et Al. Effects Of Amino Acid Derivatives On Physical, Mental, And Physiological Activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-1144.

    合成参考文献


    摘要:Thomas, A. W., Science of Synthesis, (2007) 31, 531.
    摘要:Balci, M.; Çelik, M.; Gültekin, M. S., Science of Synthesis, (2006) 28, 35.
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