2-氨基-2-脱氧糖的半乳糖基、葡萄糖基、甘露糖基和基于二糖的C-糖苷。
Galacto, gluco, manno, and disaccharide-based C-glycosides of 2-amino-2-deoxy sugars.
作者信息
Grant Laura, Liu Yan, Walsh Kenneth E, Walter Daryl S, Gallagher Timothy
机构信息
School of Chemistry, University of Bristol, Bristol BS8 1TS, UK.
出版信息
Org Lett. 2002 Dec 26;4(26):4623-5. doi: 10.1021/ol0269695.
[reaction: see text] Starting from readily available precursors, selenoglycosides derived from GalNAc, GlcNAc, and ManNAc were prepared by either a one- or a two-step process. The anomeric selenides underwent facile C-Se homolysis to provide the corresponding anomeric radicals, which were trapped with alkenes to give C-glycosides. This provides a general entry to alpha-C-glycosides based on 2-amino-2-deoxy sugars that is also applicable to disaccharide variants.
[反应：见正文] 从容易获得的前体出发，通过一步或两步法制备了源自N-乙酰半乳糖胺、N-乙酰葡糖胺和N-乙酰甘露糖胺的硒代糖苷。异头硒化物易于发生碳-硒均裂反应，生成相应的异头自由基，这些自由基被烯烃捕获生成碳苷。这为基于2-氨基-2-脱氧糖的α-碳苷提供了一种通用的合成方法，该方法也适用于二糖变体。
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