Convergent preparation of 1,6-linked C-disaccharides via olefin metathesis

Abstract

Abstract The DCC mediated coupling reaction of 3,4,6-tri- O -benzyl-1,2-dideoxy- d -arabino-hex-1-enitol ( 5a ) with a variety of sugar based carboxylic acids 6a-d gave esters 7a-d in good yield. Methylenation of the formed esters led to the acyclic enol ethers 8a-d and exposure to the Schrock molybdenum catalyst 1 in warm toluene, in the box, gave the target C -disaccharide glycals 9a-d in good yield. The 1,6-linked gluco based C -disaccharide glycal 9a was converted to the 2-deoxy-β- gluco -derivative 10a and the corresponding and gluco β- gluco-C -disaccharide 13 .