Stereoselective Synthesis of 1,1'-Disaccharides by Organoboron Catalysis

Abstract

The highly stereoselective synthesis of 1,1'-disaccharides was achieved by using 1,2-dihydroxyglycosyl acceptors and glycosyl donors in the presence of a tricyclic borinic acid catalyst. In this reaction, the complexation of the diols and the catalyst is crucial for the activation of glycosyl donors, as well as for the 1,2-cis-configuration of the products. The anomeric stereochemistry of the glycosyl donor depends on the employed glycosyl donor. Applications of the produced 1,1'-disaccharides are also described.

Keywords: carbohydrates; glycosylation; organocatalysis; total synthesis; trehalose.