DESIGN AND SYNTHESIS OF A TRISUBSTRATE ANALOG FOR ALPHA(1-]3)FUCOSYLTRANSFERASE - A POTENTIAL INHIBITOR

Phenyl 1-azido-3, yl-1-deoxy-2-seleno-alpha-L-fuco-heptulopyranoside ( 5), readily accessible from perbenzylated L-fucono-1,5-lactone, is a k ey intermediate in the preparation of trisubstrate analogue 2. NIS med iated condensation of fucosyl donor 5 with methyl 2,4,6-tri-O-benzyl-a lpha-D-glucopyranoside (7) and ensuing reduction of the azido function furnished ketodisaccharide 10b, which was elongated at the 1-amino gr oup of the fucose residue with a malonic acid spacer. The thus obtaine d compound was deprotected and subsequently coupled with 5'-amino-5'-d eoxy-guanosine to afford the target compound 2.