CONFORMATIONAL-ANALYSIS OF METHYL -ACETYL-6-DEOXY-6-PHENYLSULFINYL-ALPHA-D-GLUCOSIDE

Conformational analysis of methyl deoxy-6-(R)-phenylsulfinyl-alpha-D-g lucopyranoside (1), methyl deoxy-6-(S)-phenylsulfinyl-alpha-D-glucopyr anoside (2) and methyl l-6-deoxy-6-phenylsulfonyl-alpha-D-glucopyranos ide (3) in solution (CDCl3) and the crystalline state was carried out using H-1-NMR spectra and X-ray crystallographic data. The conformatio nal preference of the C6-S bond in the above mentioned compounds was f ound to be GT (GT is short for gauche-trans), and as a 1:1 mixture of rotamers for the (S)-S-oxide (2) and sulfone (3) but not in the (R)-S- oxide (1) in the solid state.