K. Teranishi
Apr 2, 2002
Citations
0
Influential Citations
12
Citations
Journal
Carbohydrate research
Abstract
2-O-(p-Toluenesulfonyl)sucrose was regioselectively synthesized by direct p-toluenesulfonylation of sucrose using N-(p-toluenesulfonyl)imidazole in the presence of molecular sieves at 40 degrees C. The reactivities of the sucrose hydroxy groups toward this sulfonylation increased in the order as follows: OH-2>>OH-1'>OH-3'>OH-6>OH-6'. These results were diametrically opposite to the expected sulfonylation with p-toluenesulfonyl chloride in pyridine, for which the reactivity increased in the order as follows: OH-6', OH-6>>OH-1'>OH-2. The desired 2-O-(p-toluenesulfonyl)sucrose was readily isolated by simple open reversed-phase column chromatography, followed by recrystallization, thus overcoming the main difficulties associated with regioselectivity, efficiency, and isolation techniques for the practical preparation.