Addition of diazomethane and sulfur ylides to the carbonyl group in derivatives of ketoses and aldoses-III. Reactions of 1,2-dideoxy-4,5-O-isopropylidene-d-glycero-3-pentulose

Article abstract of DOI:10.1016/0040-4020(80)88039-2

The reactions of diazomethane and dimethyloxo-sulfonium methylide with 1,2-dideoxy-4,5-O-isopropylidene-d-glycero-3-pentulose were studied. The sulfur ylide yielded two epimeric epoxides while diazomethane in addition furnished a homologous ketone. The reaction with diazomethane was carried out with varying concentrations of methanol in the reaction medium, and the relative yields of the three products were determined in each case. The results were explained on the basis of a two-step reaction mechanism proposed earlier. Steric effects and complexation between the positive nitrogen and one of the oxygens were inferred to be important.