Aziridine Ring Opening as Regio- and Stereoselective Access to C-Glycosyl-Aminoethyl Sulfide Derivatives

Abstract

A short synthetic route to stereoselective access to C-glycosyl-aminoethyl sulfide derivatives has been developed through the reaction of tributhyltin derivatives of glycals with aziridinecarboaldehyde and the regioselective ring opening of a chiral aziridine with thiophenol. The absolute configurations of the resulting diastereoisomers were determined by 1H NMR spectroscopy.

Recent advances in the accessibility, synthetic utility, and biological applications of aziridines

“…C -Glycosyl-aminoethyl sulfide derivatives ( 246–249 ) were synthesized by Zawisza et al via a reaction between tributyltin derivatives of glycals ( 234–235 ) and aziridinecarbaldehyde ( 236 ) and the regioselective ring opening of chiral aziridines ( 241–244 ) with thiophenol ( 245 ) (Scheme 43). 72 Glycoconjugates are very interesting derivatives due to their participation in many important biochemical processes.…”