Synthesis of Glycosyl Trifluoroacetates and Their Reactions with Carboxylic Acids

概要

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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.
社団法人日本薬学会の論文
1986-10-25