Glycosylation of 5-Phenyl-1,3,4-oxadiazole-2-thiol with α-D-Glucopyranosyl Chloride under Phase Transfer Conditions

V. O. Kur'yanova,# S. A. Kotlarb, U. S. Priskokaa, T. A. Chupakhinaa, and V. Ya. Chirvaa

# Phone: (0652) 23-3885; e-mail: vladimir@tnu.crimea.ua
a Vernadsky Tauric National University, pr. Vernadskogo 4, Simferopol, Autonomous Republic of Crimea, 95007 Ukraine
b Bogatsky Physicochemical Institute, National Academy of Sciences of Ukraine, Chernomorskaya doroga 86, Odessa, 270080 Ukraine

Received December 26, 2005; in final form, January 20, 2006

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 (solidľorganic solvent) conditions. The reaction rate and the ratio of the resulting N- and S-regioisomers depend on the catalyst nature.

Key words: crown ethers, glucosaminides, N- and S-glycosylation, phase transfer catalysis, 5-phenyl-1,3,4-oxadiazole-2-thiol

Russian Journal of Bioorganic Chemistry 2006, 32 (5):468-471