Sialic acids are a diverse family of more than 50 naturally occurring 2-keto-3-deoxy-nononic acids, amongst which N-acetyl neuraminic acid is the most ubiquitous.  In glycoconjugate chains, sialic acid is found at the terminal position, and is commonly attached to galactose or another sialic acid unit.  Sialic acid is involved in numerous biological functions which range from cell-cell adhesion, to cell mobility, pathogen mediation and oncogenesis.  The synthesis of sialic acid targets is essential for the design of therapeutics.  Stereoselective control of sialylations is still a challenge and therefore there are low yields of the desired target (a anomer).  Previously we reported that the use of a STol sialyl donor with at C-4 a TBDMS group can lead to a full stereocontrol for the synthesis of a(2-6) sialosides. Herein we describe the extension of this methodology for other sialyl linkages.

Expanding the scope of silyl protecting groups for sialylation reactions

245th National Meeting (2013)

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