Stereoselective synthesis of aminoacyl hepto glycosides: synthetic tools for biochemical interactions studies

Abstract

The titanium-catalysed enantioselective epoxidation of allylic alcohols, and the regioselective opening of the resulting epoxide, have been successfully applied to the chiral synthesis of a terminal α-aminoacyl glycoside of biological importance. Limitation of this route has been evidenced as a consequence of the influence of the chiral centres of the sugar on the stereo- and regio-selectivities. This synthetic route offers a new entry to the important class of terminal α-aminoacyl sugars.