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Abstract
Reaction of 1,4:3,6-dianhydro-2,5-di- O-mesyl- and -tosyl- d-mannitol with sodium azide afforded the 2,5-diazido- l-iditol derivative. The analogous d-glucitol isomer was obtained in a similar reaction starting from the corresponding d-glucitol derivatives, and showed significant, hypnotic activity. For establishing the structure-activity relationship, 1,4:3,6-dianhydro-2,5-diazido-2,5-dideoxy- l-mannitol ( 19), as well as its antipode 27, was synthesized, starting from dmannitol. Compound 19 was as effective as Doriden® (3-ethyl-3-phenylglutarimide), a well known, hypnotic drug. The antipode 27 and the bioisosteric 1(4),3(6)-dithio derivative were, however, inactive.
Published Version
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