title: [Synthesis of heteroaromatic N-beta-glycosides of N-acetylghicosamine under phase transfer conditions. III. 1,2,4-triazoIin-3-ones glucosaminides].
abstract: The catalytic phase transfer reactions of 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-a-D-glucopyranosyl chloride with thiosubstituted 4-phenyl-5-R-thio-Delta2-1,2,4-triazolin-3-ones in solid alkali-organic solvent and in aqueous alkali-organic solvent were studied. The main products ofglucosaminilation reaction are the appropriate N-beta-glucosaminides. The effect of reaction conditions on the yield and composition of products formed was elucidated on the example of the reaction alpha-D-glucosaminyl chloride with 5-methylthio-4-phenyl-Delta2-1,2,4-triazolin-3-one. The optimal conditions of phase transfer glycosylation were established. N-1,2-trans-grycosidic bond formation was proved by 1H NMR and IR data as well as a comparison with spectral data obtained previously for the glycosides of similar structure.
authors.forename: V O
authors.initials: VO
authors.lastname: Kur'ianov
authors.forename: M K
authors.initials: MK
authors.lastname: Tokarev
authors.forename: T A
authors.initials: TA
authors.lastname: Chupakhina
authors.forename: V Ia
authors.initials: VIa
authors.lastname: Chirva
mesh_terms: D000117:Acetylglucosamine / Q000031:analogs & derivatives*; D002384:Catalysis; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D015394:Molecular Structure; D044367:Phase Transition
chemical_list: D006027:Glycosides; D000117:Acetylglucosamine