In(OTf)3 efficiently activated N-phenyltrifluoroacetimidate and In(OTf)3 in combination with various halogenated reagents or PhIO promoted glycosylation using thioglycoside in good yields. The combination with iodine interhalogens (e.g., ICl or IBr) effectively promoted α-sialylation.
The potential of sialic acids as therapeutic agents has gradually been recognized due to its importance in the proper functioning of living systems, and likewise the virulence of several pathogens. However, synthesis of these compounds often result in poor yields and selectivities because of inherent characteristics associated with their structures. Use of various promoters, solvent systems and introduction of auxiliaries has since improved the outlook of chemical sialylation. Of these, attachment of various groups on C5 has notably resulted in improved α-selectivity. This mini review focuses on C5 structural modification of sialic acids over the past decade, most notably the oxazolidinone group protection.
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