EFFICIENT SYNTHESIS OF POLYLACTOSAMINE STRUCTURES THROUGH REGIOSELECTIVE GLYCOSYLATIONS[1

Abstract

Di-, tri- and tetramers of β-(1→3)-linked N-acetyllactosamine residues have been synthesised as their methyl glycosides, to be used in ITC binding studies to various galectins. The synthetic strategy involves two types of regioselective glycosylations: couplings of a galactosyl donor to 3,4-diol N-tetrachlorophthalimido glucose acceptors to give the lactosamine monomer building blocks, and subsequent formation of the oligomers through consecutive couplings of lactosamine donors to 2′,3′,4′-lactosamine acceptors, with high selectivity for the desired products.