New dipolar cycloaddition reactions of a carbohydrate-derived vinyl sulfoxide alkyne equivalent and a polymer-supported alkyne with azides /

Abstract

The attempted synthesis of a class of carbohydrate analogs known as pseudodisaccharides and the study of soluble polymer supports were the focus of this research. The potential of 1,3-dipolar cycloadditions with carbohydrate-derived vinyl sulfoxides and a sulfone with organic azides was investigated to synthesize the pseudodisaccharide. The conditions of the reaction would allow for the cycloaddition followed by the elimination of the sulfur group in a single reaction flask because of the electron withdrawing effects ofthe sulfur group. The study of soluble polymer supports utilized poly(ethyleneglycol) monomethylether to create soluble polymer-supported carbohydrates. The methodology of dipolar cycloaddition was applied to a polymersupported alkyne for the synthesis of sugar-derived triazoles.