Department of Organic Chemistry, Faculty of Chemistry, Gdańsk University of Technology, Narutowicza Street 11/12, 80-233, Gdańsk, Poland.
Nuclear Magnetic Resonance Laboratory, Faculty of Chemistry, Gdańsk University of Technology, Narutowicza Street 11/12, 80-233, Gdańsk, Poland.
Sci Rep. 2022 Oct 7;12(1):16838. doi: 10.1038/s41598-022-21174-8.
Herein, we present the application of 2-deoxy-D-glucose derivatives as chiral probes for elucidation of the absolute configuration of chiral secondary alcohols. The probes are attached to the studied molecules via glycosylation reaction and the resulting products are examined by a set of standard 2D NMR experiments. The absolute configuration of an oxymethine carbon atom binding the probe is established on a basis of a set of diagnostic dipolar couplings (NOEs/ROEs). These correlations may be considered diagnostic due to a pronounced lack of conformational freedom of the formed glycosidic linkage. While the chance for an observation of the diagnostic signals is the highest when the resulting glycoside in an α-anomer. 2-deoxy-D-glucose was selected as a probe of choice since is it known to strongly prefer the formation of α-glycosides.
在这里，我们介绍了 2-脱氧-D-葡萄糖衍生物作为手性探针在阐明手性仲醇的绝对构型中的应用。探针通过糖苷化反应与研究分子连接，然后通过一组标准的 2D NMR 实验进行检查。通过一组诊断偶极耦合（NOEs/ROEs）确定与探针结合的氧亚甲基碳原子的绝对构型。这些相关性可以被认为是诊断性的，因为形成的糖苷键的构象自由度明显受到限制。当形成的糖苷为α-异构体时，观察到诊断信号的机会最高。选择 2-脱氧-D-葡萄糖作为首选探针，因为它已知强烈倾向于形成α-糖苷。
