An efficient approach for total synthesis of aminopropyl functionalized ganglioside GM1b

A highly efficient protocol for the synthesis of aminopropyl functionalized ganglioside GM1b has been described. The full protected ganglioside GM1b was obtained in 71% yield within 5 h. The key feature of the synthetic approach was the use of sialic acid donor that was with a C-5 trichloroacetamide moiety and with a dibenzyl phosphite residue as leaving group at the anomeric carbon. The sialyl donor gave high yields and excellent α-anomeric selectivities with a wide variety of glycosyl acceptors ranging from C-3 or C-6 hydroxyls of galactoside to C-6 hydroxyl of glucosaminoside by using TMSOTf as catalyst in a mixture solution of acetonitrile and methylene chloride.