Facile Chemo-Enzymatic Synthesis of Monosaccharide Fatty Acid Esters

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Abstract
A range of monosaccharide fatty acid esters was prepared by enzymatic esterification of sugar acetals to provide a series of esters for detailed investigation of their surfactant properties. 6-O-acyl-D-galactopyranoses 2, 6-O-acyl-D-glucopyranoses 4 and 5-O-acyl-D-xylofuranoses 6 were prepared by Mucor miehei lipase catalysed esterification of 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 1a, 1,2-O-isopropylidene-α-D-glucofuranose 3a and 1,2-O-isopropylidene-α-D-xylofuranose 5a with decanoic, dodecanoic, tetradecanoic, hexadecanoic and octadecanoic acids respectively followed by cleavage of the isopropylidene group(s) of the monosaccharide acetal estes 1b-f, 3b-f and 5b-f.