Synthesis of carbohydrate haptens to be used for generation of catalytic antibodies

Article abstract of DOI:10.1080/07328309808005774

The glycoside 2-(2.-azidoethoxy)ethyl 2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside was prepared and then reacted, first with methyl phosphonyl dichloride, then with dimethylaminoethanol, to give the methylphosphonyl diester 9. N-Methylation of 9 with methyl iodide and subsequent catalytic hydrogenation gave the methylphosphonyl diester 11. The corresponding phenylphosphonyl diester 14 was also prepared in a similar way. The phosphonyl diesters 11 and 14 are analogs of the transition states for 3-O-acetylation and 3-O-benzoylation of β-D-glucopyranose derivatives with acetyl- and benzoylcholine, respectively. They will be used for generation of catalytic antibodies.