Carbohydrate-protein interactions are involved in a myriad of biological processes. Thus, glycomimetics have arisen as one of the most promising synthetic targets to that end. Within the broad variety of glycomimetics, thiodisaccharides have proven to be excellent tools to study these processes, and even more, some of them unveiled interesting biological activities. This review brings together research made on the introduction of N-acetylhexosamine residues into thiodisaccharides to date, passing through classic substitution (as S_N2, thioglycosylation and ring-opening reactions) and addition (as thiol-ene coupling and Michael-type additions) reactions. Recent and interesting developments regarding addition reactions to vinyl azides, cross-coupling reactions and novel chemoenzymatic methods are also discussed.

中文翻译：

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带有 N-乙酰己糖胺残基的硫二糖的合成：挑战、成就和前景

碳水化合物-蛋白质相互作用涉及无数的生物过程。因此，糖模拟物已成为最有希望的合成目标之一。在种类繁多的糖模拟物中，硫二糖已被证明是研究这些过程的绝佳工具，甚至其中一些还揭示了有趣的生物活性。这篇综述汇集了迄今为止关于将N-乙酰己糖胺残基引入硫二糖的研究，通过经典取代（如 S _N2、硫糖基化和开环反应）和加成（如硫醇-烯偶联和迈克尔型加成）反应。还讨论了关于乙烯基叠氮化物的加成反应、交叉偶联反应和新的化学酶促方法的最新和有趣的发展。