Synthesis of Heteroaromatic N-β-Glycosides of N-Acetylglucosamine under the Conditions of Phase Transfer Catalysis: I. Glucosaminides of 2-Oxobenzazoles

V. O. Kur’yanov1 #, T. A. Chupakhina1, A. E. Zemlyakov1, V. Ya. Chirva1, O. V. Shishkin2, S. V. Shishkina2, S. A. Kotlyar3, and G. L. Kamalov3

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1Vernadsky Tauric National University, pre. Vernadskogo 4, Simferopol, Autonomous Republic of Crimea, 95007, Ukraine
2Institute of Scintillation Materials, Scientific and Technological Complex Institute of Monocrystals, National Academy of Sciences of Ukraine, Kharkov, Ukraine
3Bogatsky 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: Glycosylation of benzothiazolone-2, 5-methylbenzoxazolone-2, and benzothiazolone-2 with the full acetate of α-D-glucosaminyl chloride in the phase transfer systems investigated (solid-organic solvent and aqueous alkali-organic solvent) regioselectively leads to the corresponding N-β-D-glucosaminides, which is proved by 1H NMR spectroscopy and X-ray analysis.

Key words: amide-imide tautomers, crown ethers, N-β-glycosylation, phase transfer catalysis, quaternary ammonium salts, regioselectivity, X-ray analysis

Russian Journal of Bioorganic Chemistry 2006, 32 (6): 552-557