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A new route for the chemical valorisation of lactose
Authors:Corsaro Antonino  Catelani Giorgio  D'Andrea Felicia  Fisichella Salvatore  Mariani Manuela  Pistarà Venerando
Institution:Università di Catania, Dipartimento di Scienze Chimiche, viale A. Doria 6, I-95125 Catania, Italy. acorsaro@dipchi.unict.it
Abstract: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.
Keywords:Aldohexos-5-uloses  cyclitols  elimination  lactose  chemical valorisation  triacetonlactose dimethyl acetal
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