Exploring the native chemical ligation concept for highly stereospecific glycosylation reactions

摘要

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_Ni mechanism was proposed and corroborated by computational calculations.