A CHROMATOGRAPHIC ANALYSIS OF THE PRODUCT FROM THE TRITOSYLATION OF SUCROSE: CRYSTALLINE 6,6′-DI-O-TOSYLSUCROSE

Abstract

Chromatographic analysis on silicic acid of the so-called "tri-O-tosylsucrose" which is formed in 95% yield on the reaction of 3 moles of p-toluenesulphonyl chloride with 1 mole of sucrose in pyridine at 0° has shown the substance to contain penta-, tetra-, tri-, and di-O-tosylsucroses in the molar ratios 0.05:0.33:1:1, respectively. Any mono-O-tosylsucrose present in the reaction mixture may have been lost in the isolation of the product. The composition of the product was substantially the same when the reaction was performed at −18°. The chromatogram separated the tritosylates into two subfractions. The major subfraction represented 29% by weight of the original "tri-O-tosylsucrose" and could be converted to 1′,2:3,6:3′,6′-trianhydrosucrose in 77.4% yield. Therefore, the so-called "tri-O-tosylsucrose" can contain only 25–29% of 1′,6,6′-tri-O-tosylsucrose. 6,6′-Di-O-tosylsucrose crystallized from the di-O-tosylsucrose fraction in 10% over-all yield.