Pandey Ram Pratap, Maheshwari Mittali, Hussain Nazar
Department of Medicinal Chemistry, Institute of Medical Sciences, Banaras Hindu University, Varanasi, 221005, India.
Chem Commun (Camb). 2023 Aug 10;59(65):9900-9903. doi: 10.1039/d3cc02423g.
A Lewis-acid-mediated highly regio- and stereoselective chiral azidation of C2-substituted glycals is reported. This strategy provides excellent, scalable, and mild reaction conditions for the stereoselective introduction of the azido group at the C3-position of various C2-substituted glycals. The reactivity of the various glycals reveals that the electron-withdrawing behavior of the C2-group is crucial for C3-selectivity. The newly installed azido group was used as a handle for the synthesis of various C3-glycoconjugates and α-chiral azido naphthalene polyols.
报道了一种路易斯酸介导的C2-取代糖烯的高度区域和立体选择性手性叠氮化反应。该策略为在各种C2-取代糖烯的C3位立体选择性引入叠氮基提供了优异、可扩展且温和的反应条件。各种糖烯的反应活性表明，C2-基团的吸电子行为对C3-选择性至关重要。新引入的叠氮基被用作合成各种C3-糖缀合物和α-手性叠氮萘多元醇的手柄。
