Department of Chemistry and Biochemistry, University of Colorado, Boulder, CO, 80309, USA.
Chem Asian J. 2018 Oct 18;13(20):2978-2990. doi: 10.1002/asia.201800971. Epub 2018 Oct 1.
Due to the central role played by carbohydrates in a multitude of biological processes, there has been a sustained interest in developing effective glycosylation methods to enable more thorough investigation of their essential functions. Among the myriad technologies available for stereoselective glycoside bond formation, dehydrative glycosylation possesses a distinct advantage given the unique properties of C1-alcohols such as straightforward preparation, stability, and a general reactivity compatible with a diverse set of reaction conditions. In this Focus Review, a survey of direct dehydrative glycosylations of C1-alcohols is provided with an emphasis on recent achievements, pervading limitations, mechanistic insights, and applications in total synthesis.
由于碳水化合物在多种生物过程中发挥着核心作用,因此人们一直致力于开发有效的糖基化方法,以更深入地研究其基本功能。在众多用于立体选择性糖苷键形成的技术中,脱水糖基化具有独特的优势,因为 C1-醇具有独特的性质,如制备简单、稳定性好以及与多种反应条件兼容的一般反应性。在这篇重点综述中,提供了 C1-醇的直接脱水糖基化反应的综述,重点介绍了最新的成就、普遍存在的局限性、反应机理和在全合成中的应用。