Trends in Glycoscience and Glycotechnology
Online ISSN : 1883-2113
Print ISSN : 0915-7352
ISSN-L : 0915-7352
Article for JSCR 40th Anniversary Issue
Boronic-Acid-Catalyzed Regioselective and Stereoselective Glycosylations via SNi-Type Mechanism
Daisuke Takahashi
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2019 Volume 31 Issue 181 Pages SE93-SE94


1,2-cis-Glycosides are frequently found in various biologically active natural products. However, the stereoselective synthesis of these glycosides is still difficult due to the lack of neighboring group participation. Therefore, the development of efficient synthetic methods has been required. In this context, we have reported novel regio- and 1,2-cis-α-stereoselective glycosylations using 1,2-anhydroglycosyl donors and diol acceptor-derived boronic ester catalysts without additives under mild conditions. In addition, development of 1,2-cis-stereoselective glycosylations using mono-ol acceptor-derived borinic esters and their application to the total synthesis of natural glycolipids were also reported. In this mini-review, further extended studies on boronic-acid-catalyzed regio- and stereoselective glycosylations are introduced.

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© 2019 FCCA (Forum: Carbohydrates Coming of Age)
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