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Carbohydrate research

Direct regioselective 2-O-(p-toluenesulfonylation) of sucrose.


PMID 11909594

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.

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