Synthesis of 1-, 6- and 1,6-derivatives of methyl D-fructofuranosides

A variety of derivatives of methyl α- and β-D-fructofuranosides modified at C1 or C6, or at C1 and C6, have been prepared in which the hydroxyl group(s) has been replaced by azido, amino, chloro, bromo, hydrogen and thiol acetate functions. These compounds were made by displacements on methyl 1,6-di-O-p-toluenesulfonyl-D-fructofuranosides, or on 2,3-O-isopropylidene-l,6-di-O-p- toluenesulfonyl-β-D-fructofuranose and subsequent glycosidation. A number of indirect methods of preparation of methyl D-fructofuranosides, mostly based on 1,3,4,6-tetra-O-benzoyl-D-fructofuranose have been investigated.