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

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

Carbohydrate Research 337(7): 613-619

ISSN/ISBN: 0008-6215

PMID: 11909594

DOI: 10.1016/s0008-6215(02)00039-3

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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Accession: 003714748

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