There are many examples of polysaccharides in natural products that contain 2-deoxy glycosides and have been found to have biological activity against a variety of cancer and microbial targets. However, 2-deoxy glycosides are difficult to synthesize selectively because they lack functionality at the C2 position. This difficulty can be overcome using an alpha tosylate intermediate at the anomeric position, which allows the reactions to be beta selective. This reaction is extremely sensitive because the alpha tosylate can be easily eliminated at temperatures over -60 °C. Many reactions have been optimized for flow chemistry because fully automated continuous flow allows for better control of conditions as well as the ability to scale over time rather than over volume. Conversion of reactions to automated flow can allow for better control of cryogenic temperatures and anhydrous conditions required, as well as reduced reaction time. Once the synthesis of these disaccharides is optimized in flow, the production of larger polysaccharide chains can be optimized. Specifically, we intend to investigate the telescoped synthesis of immunologically relevant scaffolds such as anthracycline and angucycline antibiotics.

Design of an automated continuous flow system for selective 2-deoxy glycosylations of bioactive metabolites

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