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-inositel. Therefore our synthetic strategy offers a new and simple method to transform lactose into carbocyclic monosaccharide analogues.
|Autori:||CORSARO A.; CATELANI G; D'ANDREA F.; FISICHELLA S.; MARIANI M.; PISTARÀ V.|
|Titolo:||A new route for the chemical valorisation of lactose|
|Anno del prodotto:||2003|
|Digital Object Identifier (DOI):||10.1065/ESPR2001.12.104.2|
|Appare nelle tipologie:||1.1 Articolo in rivista|