Carbohydrate-derived surfactants: synthesis and phase behaviour of methyl 4′ 6′-di-O-alkyl-β-lactosides

Abstract

In order to study the physical properties of lactose-derived surfactants, methyl 4′, 6′-di-O-hexyl-β-lactoside and methyl 4′, 6′-di-O-octyl-β-lactoside were prepared. The 4′, 6′-O-isopropylidene ketal was used as a temporary protecting group in the key intermediate. The 3′, 4′-O-benzylidene acetal was identified as a minor by-product in the preparation of methyl 4′, 6′-O-benzylidene-β-lactoside by acid-catalysed transacetalation. The phase behaviour of these derivatives is reported.