Synthetic approach towards sulfated chondroitin di-, tri- and tetrasaccharides corresponding to the repeating unit

Article abstract of DOI:10.1016/S0008-6215(97)00225-5

Chondroitin di-, tri- and tetrasaccharides, as well as their 4-, 6- mono- and 4,6-disulfates as their 4-methoxyphenyl glycosides, were systematically synthesized. Target disaccharides having βGalNAc-(1 → 4)- βGlcA sequences were obtained starting from the corresponding pivotal chondroitin disaccharide precursor. A trisaccharide intermediate, which was synthesized by coupling of glucuronate imidate with a known disaccharide acceptor, was transformed into the sulfated and non-sulfated chondroitin trisaccharides. Chondroitin tetrasaccharide and the corresponding 4- disulfate, 6-disulfate as well as 4,6-tetrasulfate were also obtained based on the strategy developed above starting from the reported tetrasaccharide having [βGalN₃-(1 → 4)-βGlcA₂] sequence.