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Stereoselective Synthesis of 1,1′‐Disaccharides by Organoboron Catalysis
Author(s) -
Izumi Sanae,
Kobayashi Yusuke,
Takemoto Yoshiji
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202004476
Subject(s) - stereoselectivity , glycosyl , chemistry , anomer , catalysis , glycosyl donor , stereochemistry , organic chemistry , combinatorial chemistry
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.