Synthesis of 5a‐α‐Tocopheryl Azide and Its Reaction to 1‐(5a‐α‐Tocopheryl)‐1,2,3‐triazols by [2+3]‐Cycloaddition

Abstract

Abstract 1,2,3‐Triazoles with 1‐position substituents, derived from α‐tocopherol (vitamin E), were synthesized by 1,3‐dipolar cycloaddition reactions of 5a‐azido‐α‐tocopheryl acetate with alkynes, and were fully analytically characterized. NMR spectra of the compounds and crystal structures of derivatives with a truncated isoprenoid side chain are presented. The tocopheryl moiety is readily cleaved in basic media, as a prerequisite for the use in delivery systems showing pH‐dependent drug release. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)