Center for Education and Research on Macromolecules (CERM), University of Liege, Chemistry Department, Sart-Tilman, Allée de la Chimie 3, Bat B6a, B-4000 Liege, Belgium.
Carbohydr Res. 2013 Oct 18;380:29-36. doi: 10.1016/j.carres.2013.07.003. Epub 2013 Jul 15.
An original and versatile method for the synthesis of a range of novel mannose-based surfactants was developed via metal-free photo-induced thiol-ene/-yne 'click' reactions. This light-mediated hydrothiolation reaction involving a thiolated mannose was successfully applied to terminal and internal alkenes, dienes, and alkynes, leading to monocatenary, branched, double-headed, and bolaform amphiphilic carbohydrate esters, respectively. A surface activity study showed that these new compounds possess valuable properties and display specific behavior at the air-water interface. It also demonstrated the greater flexibility of the thioether moiety in the spacer of the surfactants produced via a thiol-ene reaction in comparison with the triazole heterocyclic rings in similar glucose-based surfactants synthesized elsewhere by the alkyne-azide 1,3-dipolar addition.
开发了一种新颖且通用的方法，通过无金属光诱导的巯基-烯/-炔点击反应来合成一系列新型甘露糖基表面活性剂。这种涉及巯基甘露糖的光介导氢硫加成反应成功地应用于末端和内部烯烃、二烯和炔烃，分别得到单链、支链、双头和棒状两亲性碳水化合物酯。表面活性研究表明，这些新化合物具有有价值的性质，并在气-水界面表现出特定的行为。它还表明，与通过其他地方的炔烃-叠氮化物 1,3-偶极加成反应合成的类似葡萄糖基表面活性剂中的三唑杂环相比，通过巯基-烯反应生成的表面活性剂中硫醚部分在间隔基中具有更大的灵活性。
