三氟乙酸不稳定磺酸酯保护基及其在近红外荧光团合成中的应用。
A trifluoroacetic acid-labile sulfonate protecting group and its use in the synthesis of a near-IR fluorophore.
机构信息
Department of Biochemistry and Molecular Pharmacology, University of Massachusetts Medical School, 364 Plantation Street, Worcester, Massachusetts 01605, USA.
出版信息
J Org Chem. 2013 Jan 18;78(2):711-6. doi: 10.1021/jo302065u. Epub 2012 Dec 13.
Abstract
Sulfonated molecules exhibit high water solubility, a property that is valuable for many biological applications but often complicates their synthesis and purification. Here we report a sulfonate protecting group that is resistant to nucleophilic attack but readily removed with trifluoroacetic acid (TFA). The use of this protecting group improved the synthesis of a sulfonated near-IR fluorophore and the mild deprotection conditions allowed isolation of the product without requiring chromatography.
摘要
磺酸酯分子具有高水溶性，这一特性对于许多生物应用非常有价值，但也常常使它们的合成和纯化变得复杂。在这里，我们报告了一种磺酸酯保护基，它对亲核攻击具有抗性，但可以用三氟乙酸（TFA）轻易去除。该保护基的使用改进了磺酸基近红外荧光团的合成，并且温和的脱保护条件允许在无需进行色谱分离的情况下分离产物。
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