139517-75-2Relevant academic research and scientific papers
Convenient access to L-3,4,5-trioxygenated phenylalanine compounds from L-tyrosine
Zhou, Shengfeng,Zhou, Chen,Lu, Qian,Liu, Xintong,Yuan, Jie,Yu, Xinhong
, (2020/05/21)
A convenient and efficient synthesis of L-3,4,5-trioxygenated phenylalanine derivatives from L-tyrosine was developed. Dibromo phenylalanine is converted easily to bis-phenol via copper-catalyzed hydroxylation. The synthetic potential of this methodology has been demonstrated by efficient synthesis of L-3,4,5-trimethoxyphenylalanine methyl ester and one key intermediate of Trabectedin.
Trabectedin intermediate preparation method
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, (2019/10/01)
The invention discloses a trabectedin intermediate preparation method, which comprises: preparing a trabectedin intermediate (S)-2-(allyloxycarbonylamino)-3-(3,5-di(tert-butyldimethylsiloxy)-4-methoxyphenyl)propanoic acid by using tyrosine as a raw material. According to the present invention, the chiral source is directly introduced from the starting raw material, such that the use of chiral catalysis and chemical or enzymatic resolution in the reaction is avoided, the method has advantages of low production cost, high yield, easy purification, high purity and high optical purity of the obtained final product, and the like, the final product can be stored in large quantities, and the method is suitable for industrial production.
Synthesis and trypanocide activity of chloro-l-tyrosine and bromo-l-tyrosine derivatives
Pastrana Restrepo, Manuel,Galeano Jaramillo, Elkin,Martínez Martínez, Alejandro,Robledo Restrepo, Sara
, p. 2454 - 2465 (2018/10/02)
Twenty-two halogenated l-tyrosine derivatives were synthesized to examine new substances for the treatment of Chagas disease. The synthesis of these derivatives with different degree of substitution in the amino group with methyl iodide, giving primary, tertiary, and quaternary amino acids. All compounds were tested in vitro against intracellular amastigotes of Trypanosoma cruzi, and the cytotoxicity were evaluated over monocytic cell line U-937. Compound 25 was the most active against T. cruzi with a EC50 of 75.52 μM compared with benznidazole with a EC50 of 58.79 μM. Compounds 3, 4, 7, and 15 were the derivatives with the best selectivity index (SI) with values of 7.5, 8.3,12.1, and 8.6, respectively. Finally, compound 7 was the safer and the more promising derivative against T. cruzi.
An efficient synthesis of l-3,4,5-trioxygenated phenylalanine compounds from l-tyrosine
Chen, Ruijiao,Liu, Hao,Liu, Xiubing,Chen, Xiaochuan
, p. 3565 - 3570 (2013/04/24)
A new strategy for the synthesis of l-3,4,5-trioxygenated phenylalanine derivatives from l-tyrosine is developed for the first time. The approach, featuring the transformation of aryl diiodide to bis-phenol via a one-pot procedure including lithiation, boronation, and oxidation, is highly practical. By this robust protocol, N-protected l-3,5-bis(tert-butyldimethylsilyloxy)-4- methoxy-phenylalanine and l-3,4,5-trimethoxy-phenylalanine derivatives were obtained from l-tyrosine in 9 steps with 36-40% overall yields.
Application of the Suzuki Biphenyl Synthesis to the Natural Products Biphenomycin and Vancomycin
Brown, Allan G.,Crimmin, Michael J.,Edwards, Peter D.
, p. 123 - 130 (2007/10/02)
The synthesis of the unsymmetrical biphenyls 10 and 25 has been carried out by the palladium(0) catalysed coupling of the aryl boronic derivatives 5 and 20 with the aryl bromides 9 and 23 derived from (R)-4-hydroxyphenylglycine and (S)-tyrosine.In the former case unsuccessful attempts were made to bring about cyclization to compound 4 which is an analogue of the biphenyl ring system found in vancomycin.In the latter case, a variety of cyclization methods were used to give the cyclic products 34 and 35 which are analogues of the biphenomycin antibiotics.
