Attempted Synthesis of 2-Acetamido and 2-Amino Derivatives of Salacinol. Ring Opening Reactions

Abstract

The attempted synthesis of the 2-acetamido and 2-amino derivatives of salacinol, a naturally occurring glycosidase inhibitor, is described. Reaction of the protected acetamidothioarabinitol unit with the cyclic sulfate derived from L-erythritol gave the corresponding sulfonium sulfate, which underwent ring opening to give an acyclic amido sulfate. The corresponding reaction of the protected azidothioarabinitol unit with the cyclic sulfate proceeded to give the sulfonium sulfate. However, upon reduction of the azido function to an amine it formed an acyclic ammonium sulfate.