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Updated: Aug 15, 2026

High-throughput Synthesis of Carbohydrates and Functionalization of Polyanhydride Nanoparticles
Published on: July 6, 2012
Gram-scale syntheses of the (1-->3)-linked and (1-->4)-linked hyaluronan disaccharides
Sara L Adamski-Werner1, Bryan K S Yeung, Lynne A Miller-Deist
1Department of Chemistry, University of Illinois, 600 S. Mathews Ave., Urbana, IL 61801, USA.
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.
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