Synthesis of C-glycosides and N-glycosides /

Abstract

Glucose-derived C-glycosides and N-glycosides have been studied extensively in the following research. First the formation of a C-disaccharide was attempted. In the initial schemes two different glucose-derived dithiane nucleophiles were constructed. They were then treated with n-butyl lithium at - 78 °C and added to one of two electrophilic lactones. Although the formation of the desired C-disaccharides were not observed it was demonstrated that the dithiane bisphenylthiomethane by itself could be deprotonated at low temperatures and added to the different lactones forming Cglycosides. With this accomplished the synthesis of individual glycosyl amides were examined. It was determined that when a previously constructed glycosyl azide was treated with ethylenebis(diphenylphosphine) a phosphinimine ylide was formed. This intermediate readily reacted with a number of different acid chlorides to form various glycosyl amides. These synthetically formed amides were made with the intentions of starting a library of amide compounds. This library could then be referred to in future research.