Hasty Scott J, Rath Nigam P, Demchenko Alexei V
Department of Chemistry and Biochemistry, University of Missouri - St. Louis, One University Boulevard, St. Louis, MO 63121, USA.
Pure Appl Chem. 2017 Sep;89(9):1321-1331. doi: 10.1515/pac-2017-0112. Epub 2017 Apr 28.
This article describes the development of alkylated -benzimidazolyl (SBiz) imidates as versatile building blocks for chemical glycosylation. The SBiz imidates have been originally developed as a new platform for active-latent glycosylations and its utility was further extended to other common strategies for oligosaccharide synthesis. This article expands upon the utility of these compounds. We developed a general protocol for the synthesis of a series of -alkylated SBiz glycosides from -protected SBiz aglycones by Lewis acid-mediated coupling with glucose pentaacetate. The -alkylated SBiz moiety was found to be stable under strong basic conditions which allowed us to obtain both armed and disarmed -alkylated SBiz donors. These donors showed good reactivity at a variety of activation conditions, and generally provided high yields in glycosylations.
本文描述了烷基化苯并咪唑基（SBiz）亚氨酸酯作为化学糖基化通用构建模块的发展。SBiz亚氨酸酯最初是作为活性-潜伏糖基化的新平台开发的，其用途进一步扩展到寡糖合成的其他常见策略。本文扩展了这些化合物的用途。我们开发了一种通用方法，通过路易斯酸介导的与五乙酰葡萄糖偶联，从受保护的SBiz苷元合成一系列烷基化SBiz糖苷。发现烷基化SBiz部分在强碱性条件下稳定，这使我们能够获得武装和去武装的烷基化SBiz供体。这些供体在各种活化条件下表现出良好的反应性，并且在糖基化反应中通常提供高产率。
