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