Synthesis of galactosyl tetrazoles and 1,2,4-triazoles for inhibition of galectins

Abstract

This research aimed to prepare a series of naphthyl- and pyridyl-substituted C-β-D-galactopyranosyl 1,2,4-triazoles and tetrazoles for galectin inhibition. The target tetrazoles were prepared by the N-arylation of a C-b-D-galactopyranosyl tetrazole. 1,2,4-triazoles were prepared from C-galactopyranosyl formic acid in a 3 step procedure via N-acyl thioamide intermediates. Final step of the synthetic sequences was an O-deacetylation of the protected sugars.