Synthesis of 5-O-α- and -β-D-glucopyranosyl-D-glucofuranose and 5-O-α-D-glucopyranosyl-D-fructopyranose (leucrose)

Abstract

Reaction of 1,2-O-cyclopentylidene-α-D-glucofuranurono-6,3-lactone (2) with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (1) gave 1,2-O-cyclopentylidene- 5-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-α-D-glucofuranurono-6,3-lactone (3, 45%) and 1,2-O-cyclopentylidene-5-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucofuranurono-6,3-lactone (4, 38%). Reduction of 3 and 4 with lithium aluminium hydride, followed by removal of the cyclopentylidene group, afforded 5-O-α-(9) and -β-D-glucopyranosyl-D-glucofuranose (12), respectively. Base-catalysed isomerization of 9 yielded crystalline 5-O-α-D-glucopyranosyl-D-fructopyranose (leucrose, 53%).