Synthesis and Rearrangement of Epoxy Sugars
Ring-Contraction of sugar-derived epoxy alcohols, functionalised in position 1 and 6, by treatment with lithium bromide and N, N, N', N'-tetramethylurea in refluxing toluene gave enantiomerically pure a,b-unsaturated aldehydes of furanosides. O-Glycosidic epoxy alcohols gave only one, easily purified, aldehyde in approximately 30-60% yield depending on the substitution pattern. C-Glycosidic epoxy