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

Journal

RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY
Volume 32, Issue 6, Pages 552-557

Publisher

MAIK NAUKA/INTERPERIODICA/SPRINGER
DOI: 10.1134/S1068162006060082

Keywords

amide-imide tautomers; crown ethers; N-beta-glycosylation; phase transfer catalysis; quaternary ammonium salts; regioselectivity; X-ray analysis

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Glycosylation of benzothiazolone-2, 5-methylbenzoxazolone-2, and benzothiazolone-2 with the full acetate of a-D-glucosaminyl chloride in the phase transfer systems investigated (solid-organic solvent and aqueous alkali-organic solvent) regioselectively leads to the corresponding N-beta-D-glucosaminides, which is proved by H-1 NMR spectroscopy and X-ray analysis.

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