Abstract
2, 3, 4, 6-Tetra-O-acetyl-1-O-trifluoroacetyl-α-D-glucopyranose was prepared in a high yield by treating 1, 2, 3, 4, 6-penta-O-acetyl-α- or -β-D-glucopyranose with a mixture of trifluoroacetic acid and its anhydride in the presence of trifluoromethanesulfonic acid or antimony (V) fluoridegraphite catalyst. The reaction of the trifluoroacetate with some carboxylic acids afforded the corresponding 1-O-acyl-2, 3, 4, 6-tetra-O-acetyl-α-D-glucopyranoses. By a similar procedure, anomeric 1-O-trifluoroacetyl-2, 3, 5-tri-O-benzoyl- and -2, 3, 5-tri-O-acetyl-D-ribofuranose were obtained from 1-O-acetyl-2, 3, 5-tri-O-benzoyl- and 1, 2, 3, 5-tetra-O-acetyl-β-D-ribofuranose respectively, and these trifluoroacetates were allowed to react with some carboxylic acids to yield the corresponding 1-O-acyl-β-D-ribofuranose benzoates and acetates. These products were also prepared by direct fusion of 1-O-acetyl-β-D-ribofuranose benzoate and acetate with the carboxylic acids.
