Improved synthesis of n-octyl-beta-D-glucoside: a nonionic detergent of considerable potential in membrane biochemistry.

An improved synthesis for the nonionic detergent n-octyl-beta-D-glucoside (detergent 2) is described. The key modification over earlier methods is the utilization of n-octyl alcohol as the limiting reagent in the condensation between bromide 1 and n-octyl alcohol. A 60-70% overall yield of 2 is obtained without isolation of the intermediate. The beta-configuration at the anomeric carbon atom of 2 was confirmed by 100 mHz NMR spectroscopy.