Aminocyclitols. VIII. A Synthesis of Inosamines and Inosadiamines

Abstract muco-Inosamine-1, scyllo-inosamine, muco-inosadiamine-1,5 and myo-inosadiamine-1,2 have been synthesized from myo-inositol. Their structures have also been established by a study of the NMR spectra of their acetyl derivatives. When 1, 4, 5, 6-tetra-O-acetyl-3-O-mesyl-myo-inositol is treated with sodium azide in boiling aqueous 2-methoxyethanol, an azido derivative is obtained. The azido compound is hydrogenated in the presence of a catalyst and subsequently acetylated to give muco-inosamine-1. The stereochemical course of the reaction has been proposed to be an anchimeric reaction. When the analogous reaction is carried out with 2,3-di-O-mesyl-myo-inositol tetraacetate, myo-inosadiamine-1,2 or muco-inosadiamine-1,5 is obtained as the main product, depending on the solvent applied.