Synthesis of a sucrose dimer with enone tether; a study on its functionalization

Abstract

The reaction of appropriately functionalized sucrose phosphonate with sucrose aldehyde afforded a dimer composed of two sucrose units connected via their C6-positions (‘the glucose ends’). The carbonyl group in this product (enone) was stereoselectively reduced with zinc borohydride and the double bond (after protection of the allylic alcohol formed after reduction) was oxidized with osmium tetroxide to a diol. Absolute configurations of the allylic alcohol as well as the diol were determined by circular dichroism (CD) spectroscopy using the in situ dimolybdenum methodology.

Keywords

• CD-spectroscopy
• Cotton effect
• multivalent glycosystems
• osmylation
• stereoselective synthesis
• sucrose