SYNTHESIS AND BIOLOGICAL EVALUATION OF AZA-C-DISACCHARIDES - (1-]6)-LINKED, (1-]4)-LINKED, AND (1-]1)-LINKED SUGAR MIMICS

The synthesis of (1-->6), (1-->4), and (1-->1) linked aza-C-disacchari des, a novel class of glycomimetic compounds, is described. The polyhy droxylated piperidine ring was synthesized using vinyl bromide 11 as a common intermediate which was synthesized de novo from bromobenzene u tilizing the microbial oxidation metabolite bromodiol 10. A Suzuki cou pling of 11 with an alkylboron reagent derived from olefinated carbohy drate precursors via hydroboration was used to form the C-glycosidic b ond. Ozonolysis and selective reduction of the resultant carbonyl func tions served to produce the azasugar ring. Fully deprotected aza-C-dis accharides were obtained upon acidic deprotection. Biological screenin g of the title compounds against several common glycosidase enzymes as well as in vitro anti-HIV assays are reported.