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 prepared has been studied. The compound, methyl 7-((1S,3R,4R,5S,6S)-1-amino-3-hydroxymethyl-4,5,6trihydroxycyclohexyl) -6,7-dideoxy-α-D-gluco-heptopyranoside (1), is structurally related to cellobiose, but includes a crucial amino-functionality at the pseudoanomeric centre. It was prepared by 1,2-addition of the anion of methyl 6,7-dideoxy-2,3,4-tri-O-benzyl-α-D-gluco-hept-6ynopyranoside to (4R,5S,6R)-3-benzyloxymethyl-4,5,6-tribenzyloxy-2-cyclohexenone followed by stereoselective conversion of the tertiary alcohol to azide and finally reduction.