Chemical transformation of lactose into 4-O-β-d-galactopyranosyl-d-glucuronic acid (pseudolactobiouronic acid) and some derivatives thereof Original Research Article

The selective oxidation of the primary alcoholic function of the reducing unit of lactose was achieved in good overall yield (67%) starting from 2′,6′-di-O-benzyl-2,3:3′,4′-di-O-isopropylidenelactose dimethyl acetal (1) through a simple multi-step procedure based on the selective acetylation of OH-5 of 1 (methoxyisopropylation, acetylation, de-methoxyisopropylation) followed by a two-step oxidation at C-6 (TPAP-NMO then TEMPO-NaOCl) and finally, complete removal of the protecting groups.