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 lat...

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Bibliographic Details
Published in:Environmental science and pollution research international 2003-01, Vol.10 (5), p.325-328
Main Authors: Corsaro, Antonino, Catelani, Giorgio, D'Andrea, Felicia, Fisichella, Salvatore, Mariani, Manuela, Pistarà, Venerando
Format: Article
Language:English
Subjects:
Cheese
Conservation of Natural Resources
Food Industry
Lactose
Lactose - chemistry
Monosaccharides - chemical synthesis
Monosaccharides - chemistry
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Summary: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.
ISSN:0944-1344
1614-7499
DOI:10.1065/espr2001.12.104.2