H. Bazin, T. Polat, R. Linhardt
May 1, 1998
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0
Influential Citations
30
Citations
Journal
Carbohydrate Research
Abstract
Synthesis of a new class of anionic and amphoteric sucrose-based surfactants is described. Direct sulfonation of 6-O-acylsucrose using the pyridine‐sulfur trioxide complex led to a mixture of the regioisomeric monosulfates, 6-O-acyl-4 0 ‐O-sulfosucrose and 6-O-acyl-1 0 -O-sulfosucrose, while sulfonation of 1 0 -O-acylsucrose aAorded a mixture of 1 0 -O-acyl-6 0 -O-sulfosucrose and 1 0 -O-acyl-6O-sulfosucrose. The ratio of regioisomers ranged from 4.7:1.0 to 7.5:1.0, depending on reaction time and the size of the fatty acyl chain. The regiospecific synthesis of 6-O-acyl-4-O-sulfosucrose derivatives was accomplished by nucleophilic substitution of the sucrose 4,6-cyclic sulfate using various fatty acids. The amphoteric 6-alkylamino-6-deoxy-4-O-sulfosucrose surfactants were also synthesized by nucleophilic substitution of the sucrose cyclic sulfate by diAerent fatty amines. All the newly synthesized sucrose-based surfactants displayed excellent surface-active properties. # 1998 Elsevier Science Ltd. All rights reserved