Oligosaccharide synthesis is traditionally tedious and time-consuming.  During the past two decades, many innovative methods have been developed to facilitate this process.  Preferential activation of a highly reactive armed donor in the presence of a less reactive disarmed acceptor is the foundation of the popular reactivity based one-pot synthesis strategy.  However, to prepare building blocks with desired anomeric reactivities, extensive protective group manipulations must be carried out, thus lowering overall synthetic efficiency.  To solve this problem, a new pre-activation based one-pot glycosylation approach is developed for the efficient assembly of oligosaccharides independent of anomeric reactivities.  This is achieved by pre-activating the glycosyl donor, followed by sequential addition of building blocks in the same reaction flask.  Synthesis of several complex oligosaccharides by this method will be discussed.  Moreover, the results from mechanistic studies will be presented.  The pre-activation based one-pot method represents an important advance towards streamlining oligosaccharide synthesis, which can potentially evolve into a general glycosylation approach complementing the current automated solid-phase technology.

Development of pre-activation based one-pot carbohydrate synthesis methodologies

243rd National Meeting (2012)

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