SYNTHESIS OF CARBOHYDRATE HAPTENS TO BE USED FOR GENERATION OF CATALYTIC ANTIBODIES

The glycoside 2-(2-azidoethoxy)ethyl -O-benzyl-4,6-O-benzylidene-beta- D-glucopyranoside was prepared and then reacted, first with methyl pho sphonyl dichloride, then with dimethylaminoethanol, to give the methyl phosphonyl diester 9. N-Methylation of 9 with methyl iodide and subseq uent catalytic hydrogenation gave the methylphosphonyl diester 11. The corresponding phenylphosphonyl diester 14 was also prepared in a simi lar way. The phosphonyl diesters 11 and 14 are analogs of the transiti on states for 3-O-acetylation and 3-O-benzoylation of P-D glucopyranos e derivatives with acetyl-and benzoylcholine, respectively. They will be used for generation of catalytic antibodies.