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The synthesis of 13C6-labeled l-thyronine, 3,5-diiodothyronine, 3,3′,5-triiodothyroacetic acid and 3,3′,5,5′-tetraiodothyroacetic acid
Tetrahedron ( IF 2.1 ) Pub Date : 2020-06-27 , DOI: 10.1016/j.tet.2020.131352
Gregor S. Pilzak , Rutchanna M.S. Jongejan , Toine van den Bergh , Robin P. Peeters , Tommi Meulemans , Yolanda B. de Rijke

The effects of thyroid hormone metabolites (THMs) other than T3, rT3 and T4 are largely unknown, partially due to the lack of adequate methods. For adequate analysis, internal standards for all THMs are essential, but unfortunately not commercially available. Reported approaches for the synthesis of T0, 3,5-T2, TA3 and TA4 lack sensitivity and/or are not adaptable for 13C6-labeled analogues. In this paper, we describe the synthesis of four 13C6-labeled THMs, T0-13C6, 3,5-T2-13C6, TA3-13C6, TA4-13C6. Starting with 13C6-bromo-benzene, a short and versatile synthesis route was developed in which the formation of the diphenyl ether by a Chan-Lam coupling reaction was fundamental.



中文翻译:

合成13 C ^ 6 -标记的1-甲腺原氨酸,3,5- diiodothyronine,3,3',5- triiodothyroacetic酸和3,3',5,5'- tetraiodothyroacetic酸

T3,rT3和T4以外的甲状腺激素代谢物(THMs)的作用很大程度上未知,部分原因是缺乏适当的方法。为了进行适当的分析,所有THM的内部标准都是必不可少的,但不幸的是,该标准没有市售。报道的合成T 0,3,5-T 2,TA 3和TA 4的方法缺乏敏感性和/或不适用于13 C 6标记的类似物。在本文中,我们描述了四个合成13 Ç 6 -标记的三卤甲烷,T0- 13 Ç 6,3,5- T2- 13 Ç 6,TA3- 13 Ç 6,TA4- 13 Ç 6。从13开始C 6-溴苯,开发了一种短而通用的合成路线,其中通过Chan-Lam偶联反应形成二苯醚是基础。

更新日期:2020-07-28
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