| Summary: | Synthesis of stereochemically defined oligosaccharides by a series of glycosylation processes involving the reaction between a glycosyl donor and acceptor is essential to synthetic carbohydrate chemistry and glycobiology. However, despite the importance of glycosylation chemistry and the development of much sophisticated methodology, there remains no general and stereoselective procedure for the synthesis of oligo- and polysaccharides. Families of novel glycosyl donors have been conveniently synthesized from polyfluoropyridine derivatives and, in a short series of model glycosylation reactions, have shown that they offer great possibilities for the controlled stereoselective synthesis of oligosaccharide systems. In particular, their tunable reactivity offers the promise of broad ranging activity suitable for cascade synthesis. © 2007 American Chemical Society.
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