Acceptor-bound carbohydrate synthesis

Fig. 3. Acceptor-bound solid-phase carbohydrate synthesis.

Our approach to oligosaccharide synthesis relied on the acceptor-bound solid-phase method. This method formally reduces the synthesis of carbohydrates to a repetitive cycle of glycosylation and deprotection events. It was reasoned that the repetitive nature of an acceptor-bound glycosylation method rendered it ideal for automation. Therefore, we set out to investigate the potential variables in such a scheme. 

Three major strategies have been explored for the solid support synthesis of oligosaccharides and glycoconjugates. In one variation, the first carbohydrate is anchored to the support via its reducing end (see Scheme 1, Case 1). The carbohydrate bound to the solid support functions as an acceptor in the coupling event to a solution-based donor (D). In the cycle, a unique acceptor hydroxyl must be exposed... 

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