Automated Solid-Phase Oligosaccharide Synthesis Strategy

Design of an Automated Solid-Phase Oligosaccharide Synthesis Strategy 

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. 

Another important aspect of our acceptor-bound strategy was the delivery of donors in solution. In selecting donors we considered their stability, reactivity, ease of synthesis, and activation under homogeneous reaction conditions. The use of insoluble reagents (such as powdered molecular sieves) would not be compatible with an automated instrument. 

Another critical consideration was the development of an effective protecting-group strategy. We chose to employ benzyl ethers as permanent protecting groups, not to be removed during the course of intermittent deprotection events, because of their stability under moderately acidic and 

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IV. Design of an Automated Solid-Phase Oligosaccharide Synthesis Strategy. 43... 

Many strategies have been and are still being developed to access oligosaccharides by chemical synthesis. This chapter focuses on recent developments in the automated solid-phase synthesis of oligosaccharides and emphasizes the recent advances of novel microreactor techniques for carbohydrate synthesis. 

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