Two classes of gem-dimethyl 4-n-pentenyl glycosides (i.e., C2-series and C3-series) have been prepared and studied in both the glycosylation and hydrolysis manifolds utilizing NBS as the sole stoichiometric activator. These novel glycosylating agents, which are analogues of Fraser-Reid's 4-n-pentenyl glycosyl donors, show increased reactivity in side-by-side studies by virtue of the gem-dimethyl effect. Application of these donors will also be discussed. 

Novel glycosylating agents inspired by Fraser-Reid and applications thereof

239th National Meeting (2010)

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