<i>cis</i>-ANNULATION OF AN OXAZOLINE FRAGMENT TO LEVOGLUCOSENONE AND THE SYNTHESIS OF 4-SUBSTITUTED 3-AMINO-1,6-ANHYDRO-3-DEOXY-β-D-MANNOPYRANOSE

Abstract

Chiral 2-trichloromethyloxazolines 4,5-cis-annulated to a carbohydrate fragment were synthesized on the basis of levoglucosenone. The synthesized compounds were converted by acid hydrolysis into 4-substituted 3-amino-1,6-anhydro-3-deoxy-β-D-mannopyranoses. Intramolecular amination of allyl trichloroacetimidates by electrophilic reagents was used to construct the oxazoline ring. It was established that trichloroacetimidates containing an epoxide ring in α,β-positions spontaneously undergo recyclization with the formation of an oxazoline ring.

Authors: Bulat T. Sharipov, Anna N. Davidova, Farid А. Valeev