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-hexopyrano sides of thiophenol (3, 4) and the methyl ester of N-benzoyl-L-cysteine hav e 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 deriv ative, respectively. The conformation of the sugar residue and configuratio n of the anomeric centre as well as of the hydroxyimino group were establis hed on the basis of the H-1 NMR (DQF-COSY, ROESY, TOCSY) spectrometric tech niques 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. (C) 2000 Elsevier Science Ltd. A ll rights reserved.