Sialic acid-containing glycoconjugates are natural products and, for their biological functions, very important synthetic targets. Efficient synthesis (yield and stereoselectivity) of the glycosidic linkages with sialic acid is still quite challenging. The study of O-protecting groups in the mainstream of carbohydrate chemistry occupies a very important niche and represents the major venue to control reactivities and stereoselectivities of glycosyl donors. However, O-substitution of sialic acids, beyond traditional acetates, and the effect that O-substituents may have on the outcome of sialylation remains practically unknown. Recently, we showed that sialic acids bearing TBDMS and benzoyl substituents at O-4 and/or O-7 positions possess very interesting and rather unpredictable sialyl donor properties. As part of a broader investigation on the effect of O-protecting groups in sialic acid chemistry, herein we present the expansion of these studies.

Effect of O-substituents in sialylation reactions

247th National Meeting (2014)

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