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.
A new route for the chemical valorisation of lactose
CATELANI, GIORGIO;D'ANDREA, FELICIA;
2003-01-01
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-inositel. Therefore our synthetic strategy offers a new and simple method to transform lactose into carbocyclic monosaccharide analogues.File in questo prodotto:
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