Five phosphonic acid analogues of N-acetylneuraminic
acid (Neu5Ac) and
3-deoxy-d-glycero-d-galacto-2-nonulosonic acid (KDN) have been synthesized.
The synthesis was accomplished using
an indium-mediated coupling of N-acetylmannosamine or
mannose with dimethyl (3-bromopropen-2-yl)phosphonate in aqueous media. The potential of these
phosphonate acid analogues of sialic
acids as sialidase inhibitors was evaluated and found to show moderate
biological acitivities.
We have stereoselectively synthesized the analogues of the methyl β‐glycosides of (1→6)‐β‐D‐galacto‐oligosaccharides (up to tetrasaccharide), in which the interglycosidic oxygen atoms are replaced by a methylene group.
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