Six N -glycosyl benzofuran derivatives were synthesized by the catalysis of organic bases and condensation agents. The benzofuran derivatives were obtained by the reaction of various salicylaldehydes in acetone, and then hydrolyzed to the corresponding carboxylic acids. Finally, the target compounds were synthesized by acylation and the reaction conditions were optimized. The acetylcholinesterase (AChE) inhibitory activity of the desired compounds was tested using Ellman’s method. Most of the compounds showed acetylcholinesterase-inhibition activity; N -(2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2 H -pyran-3-yl)benzofuran-2-carbxamide ( 5a ) showed the best acetylcholinesterase inhibition, with an inhibitory rate of 84%.