Using helicid as a starting material, 4-β-D-allopyranosyloxy-benzaldehydeoxime (2) has been synthesized by the condensation reaction with hydroxyamine hydrochloride. Novel 4-β-D-allopyranosyloxy-α- chloro-benzaldehydeoxime (3) was synthesized by substitution reaction of 2 with t-BuOCl, and novel 3-(4-β-D-allopyranosyloxyphenyl)-4-aryl-5-aryl-1,2,4-oxadiazoline derivatives (5a～5h) have been synthesized by 1,3-dipolar cycloaddition reaction of 3 with Schiff bases 4a～4h. The new compounds 3 and 5a～5h were established by ¹H NMR, IR, and MS (HRMS) spectra. The preliminary bioassay test of 5a～5h showed that some of such compounds have good calm activity. For example, com-pounds 5g (200, 100 mg•kg^－1) and 5h (200, 100 mg•kg^－1) were better than the parent helicid.

Key words: 4-β-D-allopyranosyloxy-α-chloro-benzaldehydeoxime, helicid, 1,3-dipolar cycloaddition, synthesis, 1,2,4-oxadiazoline