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-((IS,3R,4R,5S,6S)-1-amino-3-hydroxymethyl-4,5,6-trihydroxycyclhexyl)-6,7-dideoxy-alpha-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-alpha-D-gluco-hept-6- ynopyranoside 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.