Lactose was readily transformed into thexyldimethylsilyl (3,4-O-isopropylidene-β-d-galactopyranosyl)-(1 → 4)-β-d-glucopyranoside (5); this compound served as intermediate for the generation of partially O-protected lactose building blocks required in oligosaccharide and glycoconjugate synthesis. Thus, from 5 via per-O-benzoylation, desilylation, trichloroacetimidate formation, glycosylation of the Lemieux spacer, and acid-catalyzed de-O-isopropylidenation methoxycarbonyloctyl (2,6-di-O-benzoyl-β-d-galactopyranosyl)-(1 → 4)-2,3,6-tri-O-benzoyl-β-d-glucopyranoside (12) was obtained. Regioselective benzoylation of 5 with benzoyl cyanide under various conditions afforded 3-O- (13), 2,3,2 -O- (14), 3,2 -O- (16), and 2,2 -O-unprotected (17) lactoside, respectively. De-O-isopropylidenation of 16 gave thexyldimethylsilyl (6-O-benzoyl-β-d-galactopyranosyl)-(1 → 4)-2,6-di-O-benzoyl-β-d-glucopyranoside (18), an important 2 ,3 ,4 -O-unprotected lactose derivative. Fucosylation of 13 and then de-O-isopropylidenation afforded thexyldimethylsilyl (2,6-di-O-benzoyl-β-d-galactopyranosyl)-(1 → 4)-[(3,4-di-O-acetyl-2-O-benzoyl-α-l-fucopyranosyl)-(1 → 3)]-2,6-di-O-benzoyl-β-d-glucopyranoside (21), an important fucosyllactose building block.