7252-34-8Relevant articles and documents
The synthesis and structure of the derivatives of 2-deoxy-2-hydroxyimino-D-lyxo-hexopyranosyl-L-cysteine and -thiophenol
Liberek, Beata,Konitz, Antoni,Frankowski, Ryszard,Smiatacz, Zygfryd
, p. 151 - 158 (2007/10/03)
3,4,6-Tri-O-acetyl-2-deoxy-2-hydroxyimino-β and -α-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-α-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-β-D-lyxo-hexopyranosyl]-thiophenol (3) was supported by X-ray diffraction data. Copyright (C) 2000 Elsevier Science Ltd.
Synthesis and properties of derivatives of 2-deoxy-2-hydroxyimino-D-arabino-hexopyranosyl-L-cysteine and -thiophenol
Liberek,Frankowski,Smiatacz
, p. 1153 - 1161 (2007/10/03)
3,4,6-Tri-O-acetyl-2-deoxy-2-hydroxyimino-α- and -β-D-arabino-hexopyranosides of thiophenol (3-5) as well as the methyl ester of N-benzoyl-L-cysteine (6,7) have been synthesized by condensation of 3,4,6-tri-O-acetyl-2-deoxy-2-nitroso-α-D-glucopyranosyl chloride (1) with thiophenol and the L-cysteine derivative, respectively. The glycopyranosides of thiophenol were modified at C-2 and C-3 positions to afford thiophenol derivatives with 2-deoxy-2-hydroxyamino-α-D-glucopyranosyl (13,14), 3-azido-2,3-dideoxy-2-hydroxyimmo-α-D-arabino-(8), β-D-arabino-(10), and α-D-ribo-hexopyranosyl (9) structures. The conformation of the sugar residue and configuration at the anomeric center and of the hydroxyimino group were established on the basis of the 1H, 13C, 15N NMR (DQF-COSY, TOCSY, NOESY, ROESY, HSQC, HMBC and HMBCN) spectrometric techniques and polarimetric data.