Synthesis of ethoxy-linked pseudo-disaccharides incorporating a crown ether macrocycle and lectin recognition

Six ethoxy-linked pseudo-disaccharides incorporating a non-reducing d-galactopyranosyl residue and a glucose bearing an 18-crown-6-ether were synthesized by the trichloracetimidate method. Deprotection left four novel structures from which two were tested against the galactose-specific lectin Kluyveromyces bulgaricus. Their minimum inhibitory concentration (MIC) was in the same order of magnitude as compared to previously prepared oligosaccharides without spacer.