Synthesis of N-Glycosides using Azidodeoxysugars

Abstract

The following work includes methods of synthesizing N-glycosides. The main focus is the use of azides synthesized from D-glucose and D-galactose as the precursors for the synthesis of a library of analogs that have an N-glycoside linkage that could potentially be tested for biological activity towards Staphylococcus aureus Type 5 and Type 8 capsular polysaccharides. The chemistry includes a modified Staudinger approach to be used for the synthesis of amides. Also a novel approach for the construction of 1, 2, 3-triazole-linked sugars has been studied. An investigation into one-pot conversion of non-sugar alcohols to the corresponding azides has been carried out as well as the development of chemistry mentioned above using microwave irradiation. Stereoselectivity and regiospecificity in the amide and triazole chemistry will be discussed in detail.