Synthesis of heteroaromaticN-β-glycosides ofN-acetylglucosamine under the conditions of phase transfer catalysis: I. Glucosaminides of 2-oxobenzazoles

Kur'yanov, V. O.
Chupakhina, T. A.
Zemlyakov, A. E.
Chirva, Ya. V.
Shishkin, O. V.
Shishkina, S. V.
Kotlyar, S. A.
Kamalov, G. L.

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: 26 December 2005/Accepted: 20 January 2006/

Original Russian Text © V.O. Kur'yanov, T.A. Chupakhina, A.E. Zemlyakov, V.Ya. Chirva, O.V. Shishkin, S.V. Shishkina, S.A. Kotlyar, G.L. Kamalov, 2006, published in Bioorganicheskaya Khimiya, 2006, Vol. 32, No. 6, pp. 615-620.

Russian Journal of Bioorganic Chemistry 32(6):p 552-557, December 2006. | DOI: 10.1134/S1068162006060082

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.