title: Chemical transformation of lactose into 4-O-beta-D-galactopyranosyl-D-glucuronic acid (pseudolactobiouronic acid) and some derivatives thereof.
abstract: 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.
authors.affiliation: Dipartimento di Chimica Bioorganica e Biofarmacia, Università degli Studi di Pisa, via Bonanno, 33, Italy.
authors.forename: Emanuele
authors.initials: E
authors.lastname: Attolino
authors.forename: Giorgio
authors.initials: G
authors.lastname: Catelani
authors.forename: Felicia
authors.initials: F
authors.lastname: D'Andrea
authors.forename: Leonardo
authors.initials: L
authors.lastname: Puccioni
mesh_terms: D000107:Acetylation; D002240:Carbohydrate Sequence; D005965:Glucuronates; D020723:Glucuronic Acid / Q000138:chemical synthesis*; D007785:Lactose / Q000737:chemistry*; D008969:Molecular Sequence Data
chemical_list: D005965:Glucuronates; C476482:pseudolactobiouronic acid; D020723:Glucuronic Acid; D007785:Lactose