Design and synthesis of a trisubstrate analogue for α(1 →3)fucosyltransferase: A potential inhibitor

Article abstract of DOI:10.1016/0040-4020(95)00451-D

Phenyl 1-azido-3,4,5-tri-O-benzyl-I-deoxy-2-seleno-α-1-fuco-heptulopyranoside (5), readily accessible from perbenzylated 1-fucono-1,5-lactone, is a key intermediate in the preparation of trisubstrate analogue 2. NIS mediated condensation of fucosyl donor 5 with methyl 2,4,6-tri-O-benzyl-α-d-glucopyranoside (7) and ensuing reduction of the azido function furnished ketodisaccharide 10b, which was elongated at the 1-amino group of the fucose residue with a malonic acid spacer. The thus obtained compound was deprotected and subsequently coupled with 5′-amino-5′-deoxy-guanosine to afford the target compound 2.