A new route for the chemical valorisation of lactose.
A totally protected di-O-benzyl derivative of triacetonlactose dimethyl acetal was transformed into a 4'-hexeno disaccharide by elimination of acetone with t-BuOK in DMF and subsequently in 5'-C-methoxy derivative by oxidation with MCPBA in methanol as a solvent. The hydrolysis of this latter compound affords 2,6-di-O-benzyl-L-arabino-aldohexosos-5-ulose, which by intramolecular aldol condensation with DBU gives an inosose that was stereoselectively reduced to epi-inositol. Therefore our synthetic strategy offers a new and simple method to transform lactose into carbocyclic monosaccharide analogues.
Corsaro
Antonino
A
Università di Catania, Dipartimento di Scienze Chimiche, viale A. Doria 6, I-95125 Catania, Italy. acorsaro@dipchi.unict.it
Catelani
Giorgio
G
D'Andrea
Felicia
F
Fisichella
Salvatore
S
Mariani
Manuela
M
Pistarà
Venerando
V
D002611:Cheese; D003247:Conservation of Natural Resources; D019649:Food Industry; D007785:Lactose / Q000737:chemistry*; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*
D009005:Monosaccharides; D007785:Lactose