Abstract
The synthesis of several 2-azido-2-deoxy- D-gluco- and - D-galactopyranosyl halides is described. With tetraethylammonium chloride, α-pyranosyl bromides react to give β-pyranosyl chlorides. This provides a facile method for obtaining selectively blocked halides for the synthesis of α-linked, amino sugar of oligosaccharides. The inversion reaction at the anomeric centre is shown to be of second order, corresponding to an S N2 mechanism. The rates of the inversion reactions were correlated to the 13C-n.m.r. data of C-1 of α-bromides. Within the gluco series, the 13C-n.m.r. shift of C-1 proves to be proportional to the natural logarithm of the rate constant. An analogous correlation in the galacto series could not be observed.
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