2-Deoxy sugars are an important class of carbohydrates which exist in numerous naturally occurring bioactive molecules and clinical agents and play crucial roles in their bioactivity as well as stability and solubility. Despite the importance of 2-deoxy sugar subunits, the glycosidic linkage of 2-deoxy glycosides was found to be susceptible to acid hydrolysis and enzymatic cleavage. It has been known that S-linked glycosides (thioglycosides) have similar conformation to that of parent O-glycosides and are resistant towards enzymatic cleavage and chemical degradation. In addition, thioglycosides are tolerated by most biological systems. Therefore, they can be employed as important tools for structural biology and attractive therapeutic agents.  In this presentation, we have described an umpolung reactivity-based stereoselective synthesis of S-linked 2-deoxy glycosides employing 2-deoxy glycosyl lithium donors and sugar-derived disulfide acceptors. This newly developed methodology has also been successfully applied in stereoselective synthesis of a complex S-linked 2-deoxy trisaccharide.

Umpolung reactivity in stereoselective synthesis of S-linked 2-deoxy glycosides

246th National Meeting (2013)

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