These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
3 files

Fluoride Migration Catalysis Enables Simple, Stereoselective, and Iterative Glycosylation

submitted on 27.08.2019, 13:50 and posted on 28.08.2019, 17:19 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.


National Institutes of Health U01GM125274


Email Address of Submitting Author


University of Michigan



ORCID For Submitting Author


Declaration of Conflict of Interest

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