Some Aspects of the Reaction of Methyl 4,6-O-benzylidene-α-D-glucopyranoside 2,3-Carbonate with 1-Dodecanol: Novel Non-Ionic Surfactants

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Abstract
The reaction of methyl 4, 6-0-benzylidene-α-D-glucopyranoside 2, 3-cyclic carbonate (2) with 1-dodecanol in the presence of a catalytic amount of triethylamine to yield the 2-O-and the 3-O-alkoxycarbonyl esters 5 and 6 is described. Catalytic hydrogenation of 5 and 6 gave the deprotected mono-esters 3 and 4 which are of interest as potential non-ionic surfactants. The corresponding ethoxycarbonyl esters 7 and 8 were also prepared and their possible role as intermediates in the formation of 2 is discussed.