Synthesis of di- and trisaccharides incorporating a crown ether macrocycle

Di- and trisaccharides incorporating a non-reducing hexopyranose residue linked to a sugar bearing a 18-crown-6-ether were synthesized by the trichloroacetimidate method. Mainly β-glycosides were isolated when secondary alcohols were used as acceptors in the presence of (C2H5)2O·BF3. Deprotection left four novel structures which were on one hand able to complex cationic species and on the other hand were able to be recognized by lectins. They are the first representatives of a new class of water-soluble cation vectors.