In recent years, the thioglycoside approach for chemical glycosylation has evolved into a very robust methodology for oligosaccharide synthesis.1 Thioglycosides are easily accessible from a variety of simple precursors and can withstand many reaction conditions associated with protecting group manipulations. This class of glycosyl donors can typically be glycosidated under a range of relatively mild activation conditions. All listed are important traits for both glycoside and oligosaccharide synthesis that are rarely found all in one class of a leaving group. Recently, were reported that the S-indolyl (SIn) leaving group further enhances utility of this method of glycosylation. The SIn leaving group showed good stability towards protecting group manipulations, but can be readily activated for glycosylation in the presence of silver carbonate and trimethylsilyl trifluoromethanesulfonate (Ag2CO3/TMSOTf).2 This unusual promoter system has allowed to achieve orthogonality with other sulfur-based leaving groups while uncovering unique reaction pathways by which the activation of the SIn group takes place. Capitalizing on our previous success, presented herein are our subsequent steps towards the development of more versatile leaving groups derived from the basic SIn glycoside scaffold.

Indolyl thioglycosides as effective building blocks for chemical glycosylation

ACS Spring Meeting 2021

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