Despite a number of advantageous properties of anomeric alcohols in glycosylation reactions, the use of these donors has been restricted to a specific class of substrates due to a lack of general coupling methodologies. Our laboratory has recently discovered cyclic phosphonium anhydrides generated from phosphine bis-oxides as powerful glycosylating reagents for the reactions of C1-hemiacetals with a variety of O-, C-, N-, and S-nucleophiles. The utility of this protocol was demonstrated in reactions with pyranoses and furanoses, which could be glycosylated in excellent yields and selectivities. Detailed NMR studies showed that the stability of cyclic intermediates formed upon the mixing of anomeric alcohols with phosphonium anhydrides controls the reactivity of the glycosyl donors. Details of this glycosylation methodology as well as mechanistic studies will be disclosed in this presentation.

New dehydrative glycosylation with phosphonium anhydrides

249th National Meeting (2015)

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