Part I: The large-scale synthesis of hyaluronan disaccharides utilizing a mild cleavage of 2-amino-2-deoxy-D-glucoside methoxycarbonyl derivatives with methyltrichlorosilane and the application for the synthesis of carbohydrate polymers. Part II: The s

The large scale syntheses of two hyaluronan disaccharides are described. Construction of the disaccharides was achieved utilizing an imidate donor and TMS-OTf as the promoter. The acetamide installation was achieved using a novel mild cleavage of 2-amino-2-deoxy-D-glucoside methoxycarbonyl derivatives with methyltrichlorosilane followed by acetylation of the free amine in yields ranging from 54%–93%. The kinetics and mechanism of the carbamate cleavage were further investigated with the use of a reactIR. The methods employed for the large-scale syntheses of the hyaluronan disaccharides were utilized for the synthesis of a disaccharide monomer containing a p-nitrophenyl carbamate functionality. Treatment of the monomer with NaH and Et₃N will result in a polymerization of the disaccharide monomer.; A better understanding of the solution behavior of carbohydrates, specifically the investigation into their hydrophobicity, would allow for a better understanding of the carbohydrate interactions occurring at a cellular level. The syntheses of model compounds incorporating a hydrophobic pyrene scaffold symmetrically tethered to carbohydrate moieties were completed. The carbohydrate moieties integrated a β-D-glucose functional group coupled to a p-nitrophenyl carbamate with varying alkyl chain lengths and were tethered to a pyrene core through a urea linkage installed to provide water solubility.