236413-33-5Relevant academic research and scientific papers
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.
