Copper-free huisgen 1,3-dipolar cycloaddition to 3-benzotriazolo-3-deoxy-β-D-galactopyranoside : Cyclization of a galactopyranoside azide and benzyne
Methyl 2-O-acetyl-3-benzotriazolo-4,6-O-benzylidene-3-deoxy- β -D-galactopyranoside was assembled by reacting benzyne, from 2-trimethylsilyl-trifluoromethansulfonylbenzene, and a secondary galactopyranoside azide in a copper-free Huisgen 1,3-dipolar cycloaddition. Following deprotection, the resulting benzotriazoles were evaluated as galectin inhibitors resulting in a 2-4 fold increase in affinity
