Glycosylation of 5-phenyl-1,3,4-oxadiazole-2-thiol with α-D-glucopyranosyl chloride under phase transfer conditions


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Abstract

5-Phenyl-1,3,4-oxadiazole-2-thiol is glycosylated easily and in high yields with 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride in the presence of catalytic amounts of aliphatic and aromatic crown ethers under phase transfer (solid-organic solvent) conditions. The reaction rate and the ratio of the resulting N-and S-regioisomers depend on the catalyst nature.

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