Synthesis of 1,6-anhydro-2,3-di- O-benzoyl-4- O-(methyl 2,3,4-tri- O-benzoyl-α- l-idopyranosyluronate)-β- d-glucopyranose from cellobiose

Abstract

The title compound ( 21) was synthesized from cellobiose as a synthon of a heparin-related oligosaccharide. The per- O-benzyl and per- O-benzoyl derivatives of 1,6-anhydro-4- O-(6-deoxy-β- d- xylo-her-5-enopyranosyl)-β- d-glucopyranose were treated with a nonsolvated borane to give a 1:2 mixture of the corresponding 4- O- α- l-idopyranosyl- and 4- O-β- d-glucopyranosyl- d-glucopyranose derivatives in total yields of 90 and 39%, respectively. Jones oxidation of 1,6-anhydro-2,3-di- O-benzoyl- 4- O-(2,3,4-tri- O-benzoyl-α- l-idopyranosyl)-β- d-glucopyranose and 1,6-anhydro-2,3- di- O-benzoyl-4- O-(2,3,4-tri- O-benzoyl-β- d-glucopyranosyl)-β- d-glucopyranose gave the corresponding uronic acid derivatives, namely, the α- l-idopyranosyluronate ( 21) and the β- d-glucosyluronate, in good yields.