The synthesis and structure of the derivatives of 2-deoxy-2-hydroxyimino-D-lyxo-hexopyranosyl-L-cysteine and -thiophenol.
3,4,6-Tri-O-acetyl-2-deoxy-2-hydroxyimino-beta and -alpha-D-lyxo-hexopyranosides of thiophenol (3, 4) and the methyl ester of N-benzoyl-L-cysteine have been synthesised by condensation of 3,4,6-tri-O-acetyl-2-deoxy-2-nitroso-alpha-D-galactopyranosyl chloride with thiophenol and the L-cysteine derivative, respectively. The conformation of the sugar residue and configuration of the anomeric centre as well as of the hydroxyimino group were established on the basis of the 1H NMR (DQF-COSY, ROESY, TOCSY) spectrometric techniques and polarimetric data. Additionally, the structure of S-[3,4,6-tri-O-acetyl-2-deoxy-2-(Z)-hydroxyimino-beta-D-lyxo -hexopyranosyl]-thiophenol (3) was supported by X-ray diffraction data.
Liberek
B
B
Faculty of Chemistry, University of Gdańsk, Poland.
Konitz
A
A
Frankowski
R
R
Smiatacz
Z
Z
D002236:Carbohydrate Conformation; D003837:Deoxy Sugars / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008958:Models, Molecular; D010091:Oximes / Q000138:chemical synthesis*; D010636:Phenols / Q000138:chemical synthesis*; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis*; D013696:Temperature; D013865:Thioglycosides / Q000138:chemical synthesis* / Q000737:chemistry; D014961:X-Ray Diffraction
C415642:2-deoxy-2-hydroxyimino-lyxo-hexopyranosyl-cysteine; D003837:Deoxy Sugars; D010091:Oximes; D010636:Phenols; D013438:Sulfhydryl Compounds; D013865:Thioglycosides