Abstract
Reactions of acetylated 1-bromo-1-deoxy-glycopyranosyl cyanides of β- d- galacto ( 2) and α- d- arabino ( 12) configurations with silver fluoride in acetonitrile at room temperature gave the corresponding 1-deoxy-1-fluoroglycopyranosyl cyanides ( 5 and 13, respectively) with inversion of the anomeric centre. Under similar conditions the β- d- gluco ( 1) and β- d- xylo ( 3) compounds resulted in the corresponding inverted 1-fluoroglycosyl cyanides ( 4 and 6, respectively) together with significant amounts of 1-cyano-2-hydroxy-glycals ( 9 and 10, respectively). Silver tetrafluoroborate in toluene at room temperature converted 2 and 3 into the 1-fluoroglycosyl cyanides ( 7 and 8, respectively) of retained anomeric configuration. 1-Chloro-1-deoxy-α- d-galactopyranosyl cyanide ( 11) also gave 7 with silver fluoride in acetonitrile at reflux temperature. Conformational equilibria of the 1-deoxy-1-fluoro-pentopyranosyl cyanides 6, 8, and 13 reflect counteraction of the anomeric effects exerted by the fluorine and the cyano group. 1-Deoxy-1-fluoro-α- d-galactopyranosyl cyanide proved to be a weak competitive inhibitor if E. coli β- d-galactosidase (K i = 2 mM).
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