New class of carbohydrate-based nonionic surfactants: diblock co-oligomers of tri-O-methylated and unmodified cello-oligosaccharides

Abstract

Mixtures of diblock co-oligomers of tri-O-methylated and unmodified cello-oligosaccharides have been found to be amphiphilic, as reported before. In order to clarify their accurate amphiphilic property, diblock co-oligomers of tri-O-methylated and unmodified cello-oligosaccharides with monodispersity, methyl β-d-glucopyranosyl-(1→4)-2,3,6–tri-O-methyl-β-d-glucopyranosyl-(1→4)-2,3,6–tri-O-methyl-β-d-glucopyranosyl-(1→4)-2,3,6-tri-O-methyl-β-d-glucopyranosyl-(1→4)-2,3,6-tri-O-methyl-d-glucopyranoside (1, pentamer), methyl β-d-glucopyranosyl-(1→4)- β-d-glucopyranosyl-(1→4)-2,3,6-tri-O-methyl-β-d-glucopyranosyl-(1→4)-2,3,6-tri-O-methyl-β-d-glucopyranosyl-(1→4)-2,3,6-tri-O-methyl-β-d-glucopyranosyl-(1→4)-2,3,6-tri-O-methyl-d-glucopyranoside (2, hexamer), and methyl β-d-glucopyranosyl-(1→4)-2,3,6-tri-O-methyl-β-d-glucopyranosyl-(1→4)- 2,3,6-tri-O-methyl-d-glucopyranoside (3, trimer) were synthesized independently. These compounds had higher surface activities compared to the mixture of diblock co-oligomers of tri-O-methylated and unmodified cello-oligosaccharides and commercially available methylcellulose (MC) SM-4. This paper describes the methods of synthesis of these compounds, and the influence of amphiphilic character on their surface activity. A new class of carbohydrate-based nonionic surfactant without long alkyl chain was discovered.