SYNTHESIS OF THE FIRST PSEUDOSUGAR-C-DISACCHARIDE - A POTENTIAL ANTIGEN FOR ELICITING GLYCOSIDE-BOND FORMING ANTIBODIES WITH CATALYTIC GROUPS

A number of synthetic routes to the first pseudo-C-disaccharide ever p repared has been studied. The compound, methyl clhexyl)-6,7-dideoxy-al pha-D-gluco-heptopyranoside (1), is structurally related to cellobiose , but includes a crucial amino-functionality at the pseudoanomeric cen tre. It was prepared by 1,2-addition of the anion of methyl 7-dideoxy- 2,3,4-tri-O-benzyl-alpha-D-gluco-hept-6- ynopyranoside to benzyloxymet hyl-4,5,6-tribenzyloxy-2-cyclohexenone followed by stereoselective con version of the tertiary alcohol to azide and finally reduction.