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Various O-alkyl glycosides were obtained in a highly stereospecific manner with retention of configuration at the anomeric center. Our method has customized native chemical ligation concept for glycoconjugates synthesis, utilizing a meticulously controlled activating system. To explain the origin of stereoselective preference, an S(N)i mechanism was proposed and corroborated by computational calculations.


Kim Le Mai Hoang, Yaguang Bai, Xin Ge, Xue-Wei Liu. Exploring the native chemical ligation concept for highly stereospecific glycosylation reactions. The Journal of organic chemistry. 2013 Jun 7;78(11):5196-204

PMID: 23638656

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