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Stereoselective Synthesis of 1,1′‐Disaccharides by Organoboron Catalysis
Authors:Sanae Izumi  Yusuke Kobayashi  Yoshiji Takemoto
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
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