Synthesis of branched and linear 1,4-linked galactan oligosaccharides

We report the synthesis of linear and branched (1→4)- d -galactans. Four tetrasaccharides and one pentasaccharide were accessed by adopting a procedure of regioselective ring opening of a 4,6- O -naphthylidene protecting group followed by glycosylation using phenyl thioglycoside donors. The binding of the linear pentasaccharide with galectin-3 is also investigated by the determination of a co-crystal structure. The binding of the (1→4)-linked galactan to Gal-3 highlights the oligosaccharides of pectic galactan, which is abundant in the human diet, as putative Gal-3 ligands. Strategic naphthylidine protection allows for the rapid assembly of linear and branched 1,4-galactans.