Abstract
The conformational behaviour of a representative azaheterocycle/thiosugar hybrid: 6-S-( benzoxazol-2- yl)-6- deoxy-1,2:3,4- di-O- isopropylidene-6- thio-α- d- galactopyranose , 1, has been characterised by X-ray crystallography, molecular modelling and NMR studies. The crystal of 1 (C 19H 23NO 6S) belongs to the monoclinic space group P2 1, with α = 8.4330(4), b = 10.287(3), c = 11.417(4) A ̊ , β = 101.66(5)°, V = 970.0(5) A ̊ 3 , and Z = 2. The structure has been determined by X-ray diffraction at 299 K using an area detector. Least-squares refinement based on 2352 reflections yielded a final wR2 of 0.098, with R1 = 0.040 [for 2210 reflections with F o > 4 σ( F o )]. The pyranose ring adopts a conformation between that of the screw-boat, O S 5, and the twist-boat, O T 2 forms. Proton NMR chemical shifts have been assigned by measurement of ID and 2D spectra. The C-5-C-6 conformer populations in CDC1 3 solution have been estimated. In parallel, a
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