title: Gram-scale syntheses of the (1-->3)-linked and (1-->4)-linked hyaluronan disaccharides.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Illinois, 600 S. Mathews Ave., Urbana, IL 61801, USA.
authors.forename: Sara L
authors.initials: SL
authors.lastname: Adamski-Werner
authors.forename: Bryan K S
authors.initials: BK
authors.lastname: Yeung
authors.forename: Lynne A
authors.initials: LA
authors.lastname: Miller-Deist
authors.forename: Peter A
authors.initials: PA
authors.lastname: Petillo
mesh_terms: D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D006820:Hyaluronic Acid / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D004187:Disaccharides; D006820:Hyaluronic Acid