Gram-scale syntheses of the (1 → 3)-linked and (1 → 4)-linked hyaluronan disaccharides Original Research Article

The first gram-scale syntheses of two hyaluronan disaccharides are described. Construction of the (1 → 4)-linked disaccharide 12 was achieved in 12% overall yield using 2,3-bis-dimethyl acetal protection in combination with chlorosilane-induced carbamate cleavage methodologies. The uronic acid functionality was installed using TEMPO oxidation with NaOCl as the hypochlorite source. The (1 → 3)-linked disaccharide 18 was achieved in 7% overall yield utilizing acetonide protection in addition to the chlorosilane-induced carbamate cleavage methodology and the TEMPO oxidation.