title: [A synthesis of heteroaromatic S- and N-beta-glycosides of N-acetylglucosamine under phase transfer conditions].
abstract: The use of crown ethers for a phase transfer-catalyzed synthesis of heteroaromatic glycosides of N-acetylglucosamine was studied. The solid-liquid system and the catalysis by 15-crown-5 were found to provide for both a 100% conversion of the alpha-D-glucosaminyl chloride peracetate and a high reaction rate. The interaction of alpha-D-glucosaminyl chloride peracetate and oxadiazole and triazole mercapto derivatives capable of thiol-thione tautomerism carried out at room temperature in acetonitrile in the presence of anhydrous potassium carbonate and crown ethers was shown to lead to both S- and N-glycosides. The structures of the compounds synthesized were confirmed by X-ray analysis and 13C and 1H NMR spectroscopy.
authors.forename: V O
authors.initials: VO
authors.lastname: Kur'ianov
authors.forename: T A
authors.initials: TA
authors.lastname: Chupakhina
authors.forename: A E
authors.initials: AE
authors.lastname: Zemliakov
authors.forename: V Ia
authors.initials: VIa
authors.lastname: Chirva
authors.forename: O V
authors.initials: OV
authors.lastname: Shishkin
authors.forename: S V
authors.initials: SV
authors.lastname: Shishkina
authors.forename: S A
authors.initials: SA
authors.lastname: Kotliar
authors.forename: G L
authors.initials: GL
authors.lastname: Kamalov
mesh_terms: D000117:Acetylglucosamine / Q000737:chemistry*; D002384:Catalysis; D043844:Crown Ethers / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D043844:Crown Ethers; D006027:Glycosides; D006571:Heterocyclic Compounds; D000117:Acetylglucosamine