Regio - and stereoselective synthesis of the iminosugars – 4-substituted 1-benzylpiperidine-3,5-diols

Abstract

We report a new approach to preparing iminosugars -4-substituted 1-benzylpiperidin-3,5-diols by reaction of 1-benzyl-4,5-epoxypiperidine-3-ols in the presence of lithium perchlorate. This regio-and stereoselective synthesis proceeds via successive nucleophilic cleavage of 1-benzyl-4,5-epoxypiperidin-3-ols by benzylamine, thiophenol and diallylamine. Initial 1-benzyl-4,5-epoxypiperidin-3-ols were obtained by oxidation of trifluoroacetates of 1-benzyl-1,2,3,6-tetrahydropyridin-3-ols.