Chemical glycosylation reactions typically require air- and water- sensitive reagents, extremely strong acids, toxic heavy metal salts, and/or ultra low temperatures to run.  As a result, the chemical synthesis of carbohydrates requires extensive synthetic training to successfully execute.  Here we present new conditions for room temperature chemical glycosylation reactions using air- and water-stable iodonium salt promoters.  The reaction setup is trivial, and extensive drying of reagents and solvents is not necessary.  We envision that this approach will one day allow chemical biologists to routinely prepare their own carbohydrate libraries, as they do with peptides today.  The scope of the reaction and its use in diastereoselective glycosylation reactions will be discussed.

Facile glycosylation reactions using air- and water-stable iodonium salt promoters

247th National Meeting (2014)

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