N-acetylneuraminic acid is the most abundant member of the sialic acid family. Its biological importance, as terminal component of glycoconjugates, ranges from cell-cell interactions to pathogens attacks, to oncogenesis. Chemical sialylations are perhaps one of the most challenging glycosylation reactions in carbohydrate synthesis, due to the structural features of sialic acid. Thus, high yields, with a complete stereocontrol on a wide variety of building blocks, is still a synthetic goal in the field. Our recent finding on the existence of a conformational equilibrium at the oxacarbenium ion level suggested that position C-4 might be relevant in sialylation reactions. In light of recent reports by Demchenko et. al on Hydrogen-bond-mediated aglycone delivery (HAD), we report herein the synthesis and testing of C-4 Picoloyl protected sialyl donors .

Applying hydrogen-bond-mediated aglycone delivery (HAD) in sialylations: Scope and limitations

251st National Meeting (2016)

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