Synthesis of 2-deoxy-2-fluoro-glucotropaeolin, a thioglucosidase inhibitor

SN2-Displacement of the anomeric bromine atom in 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-d-glucopyranosyl bromide with the tetrabutylammonium salt of triphenylmethanethiol afforded the corresponding trityl 1-thio-β-d-glucoside which led to the fully protected S-acetyl-2-fluoro-1-thio-β-d-glucose derivative, and then to the free thiol 5 by selective S-deacetylation at low temperature. 2-Fluoro-glucotropaeolin (1) was obtained by a conventional procedure from 5.