A totally protected di-O-benzyl derivative of tri-acetonlactose 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.
|Titolo:||A New Route for the Chemical Valorisation of Lactose|
|Data di pubblicazione:||2003|
|Citazione:||A New Route for the Chemical Valorisation of Lactose / CATELANI G; CORSARO A; D'ANDREA F; FISICHELLA S; MARIANI M; PISTARA' V. - In: ENVIRONMENTAL SCIENCE AND POLLUTION RESEARCH INTERNATIONAL. - ISSN 0944-1344. - 10(2003), pp. 325-328.|
|Appare nelle tipologie:||1.1 Articolo in rivista|