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Direct synthesis of anomeric tetrazolyl iminosugars from sugar-derived lactams
Beilstein Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2021-01-13 , DOI: 10.3762/bjoc.17.12
Michał Mateusz Więcław , Bartłomiej Furman

Herein we present the direct asymmetric synthesis of tetrazole-functionalized 1-deoxynojirimycin derivatives from simple sugars via a Schwartz’s reagent-mediated reductive amide functionalization followed by a variant of the Ugi–azide multicomponent reaction. The anomeric configurations of two products were unambiguously confirmed by X-ray analysis. This work also describes examples of interesting further transformations of the title products. Finally, some surprising observations regarding the mechanism of their formation were made.

中文翻译:

由糖衍生的内酰胺直接合成异头四唑基亚氨基糖

在这里,我们介绍了通过Schwartz试剂介导的还原性酰胺功能化,然后是Ugi-叠氮化物多组分反应的一种变体,从简单的糖中直接直接不对称合成四唑官能化的1-deoxynojirimycin衍生物。通过X射线分析清楚地证实了两种产物的端基异构体构型。这项工作还描述了一些有趣的标题产品转换示例。最后,就其形成机理做了一些令人惊讶的观察。
更新日期:2021-01-13
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