Sialic acid containing glycoconjugates are important synthetic targets due to their numerous biological proprieties, ranging from pathogen invasion, to cell-cell recognition. The synthesis of the natural glycosidic linkage (alpha) is one of the most challenging in the field, and often the concomitant synthesis of the unnatural product (beta) as well as the 2,3 dehydroderivative cause sialylation reactions to proceed with poor yield and lack of stereocontrol. Recently we reported the activating and alpha stereodirecting effect of a picoloyl group at C-4 in the presence of an excess of triflic acid. Herein we report the synthesis and testing of thiosialosides mono picoloylated at the glycerol chain.

Synthesis and Testing of monopicoloylated thiosialosides

2019 Spring National Meeting

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