Abstract The potential enzyme inducer, 4-S-β-d-galactopyranosyl-4-thio-d-glucopyranose, thiolactose (20), was synthesized via two routes. The intermediate, methyl 2, 3, 6-trio-O- benzoyl-4-S-cyano-4-thio-α-d-glucopyranoside (5), was obtained in high yield from methyl α- d-galactopyranoside. Reaction of the sodium salt of methyl 4-thio-α-d-glucopyranoside, derived from 5, with 2, 3, 4, 6-tetra-O-acetyl-α-d-galactopyranosyl bromide in ...