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Fluoride Migration Catalysis Enables Simple, Stereoselective, and Iterative Glycosylation

preprint
submitted on 27.08.2019 and posted on 28.08.2019 by Girish Sati, Joshua Martin, Yishu Xu, Tanmay Malakar, Paul M. Zimmerman, John Montgomery
Challenges in the assembly of glycosidic bonds pose a bottleneck in enabling the remarkable promise of advances in the glycosciences. We report a strategy that applies unique features of electrophilic boron catalysts in addressing current limitations of methods in glycoside synthesis. The strategy utilizes glycosyl fluoride donors and silyl ether acceptors while tolerating the Lewis basic environment found in carbohydrates. The method allows a simple setup at room temperature while utilizing catalyst loadings as low as 0.5 mol %, and air- and moisture stable forms of the catalyst are found to be effective. These characteristics enable a wide array of glycosylation patterns to be accessed, including all four C1-C2 stereorelationships, and the method allows one-pot, iterative glycosylations to generate oligosaccharides directly from monosaccharide building blocks.

Funding

National Institutes of Health U01GM125274

History

Email Address of Submitting Author

jmontg@umich.edu

Institution

University of Michigan

Country

USA

ORCID For Submitting Author

0000-0002-2229-0585

Declaration of Conflict of Interest

The University of Michigan has submitted a provisional patent application based on this work.

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