[A synthesis of heteroaromatic S- and N-beta-glycosides of N-acetylglucosamine under phase transfer conditions].
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.
Kur'ianov
V O
VO
Chupakhina
T A
TA
Zemliakov
A E
AE
Chirva
V Ia
VIa
Shishkin
O V
OV
Shishkina
S V
SV
Kotliar
S A
SA
Kamalov
G L
GL
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
D043844:Crown Ethers; D006027:Glycosides; D006571:Heterocyclic Compounds; D000117:Acetylglucosamine