Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 33, Pages 14054-14059Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202004476
Keywords
carbohydrates; glycosylation; organocatalysis; total synthesis; trehalose
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Funding
- JSPS KAKENHI [16H06384]
- JSPS [17J08174]
- Grants-in-Aid for Scientific Research [17J08174] Funding Source: KAKEN
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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.
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