Herein, we demonstrate the versatility of 4-aryl-3-butenylthioglycosides (ABTGs) as donors for O-glycosylation under conditions that activate the remote styrene double bond. Initial work in this area demonstrated that ABTGs could be activated for O-glycosylation using visible light irradiation in the presence of Umemoto’s reagent Mechanistic studies suggest that generation of a visible-light-absorbing electron donor-acceptor (EDA) complex between Umemoto's reagent and the ABTG styrene moiety is necessary for activation. This method of activation is orthogonal to aryl- and alkylthioglycosides, and the sulfur plays an important role in activation. Our continuing studies have demonstrated that ABTGs can be activated at room temperature for O-glycosylation under protic and Lewis acid catalysis. In addition, they have a long shelf life and are compatible with a number of transformations used in the elaboration of carbohydrate-containing molecules. As such, ABTGs provide an elusive combination of glycosyl trichloroacetimidate-like reactivity and thioglycoside stability.

O-Glycosylation using a versatile remote activation strategy

256th National Meeting (2018)

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