Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
Treatment of methyl 2,3-di-O-acyl-D-glycopyranosides 1 of glucose and mannose with catalytic amounts of trifluoromethanesulfonic acid afforded the corresponding bis(5-O-acyl-3,6-anhydro-D-glycofuranose) 1,2′:2,1′-dianhydrides 6 in 12-58% yield the structure of which was confirmed for the α-D-glucose derivative 6a by an X-ray analysis. In addition, in the presence of methyl pyruvate (2a) or methyl 2-acetoxy-acrylate (2b) various amounts of diastereomeric 3,6-anhydro-5-O-benzoyl-1,2-O-(1-methoxycarbonyl)ethylidene-α-D-glucofuranoses 5 and acylated methyl α-D-glucopyranosides 3 and 4, respectively, were formed.
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