Currently, it is very difficult to make synthetic vaccines on large scales and reduce their production cost for broader distribution. Nowadays, synthetic strategies are based upon numerous protection/deprotection steps which are time-consuming, non-economical by adding unnecessary atoms and often using toxic chemicals. We propose to develop a novel synthetic approach to prepare polysaccharides in a concise, scalable and green way. We designed directing-protecting groups which are predicted to protect one hydroxyl group and influence the regioselectivity of a variety of chemical reactions (e.g., acetylation, benzoylation, pivaloylation, silylation and glycosylation) on one of the three other unprotected hydroxyl groups. In the case of a glycosylation with glucose, we obtained a single disaccharide over six possible, significantly improving the regio- and stereoselectivity of this reaction. Furthermore, we are currently expanding this concept to other carbohydrates (mannose, galactose�) and developing an efficient method using a catalytic amount of a noncovalent directing-protecting group.

Novel strategy for carbohydrate-based synthetic vaccines

244th National Meeting (2012)

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