Open Access Open Access  Restricted Access Subscription Access

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

Булат Т. Шарипов, Анна Н. Давыдова, Фарид А. Валеев
Cover Image

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


Keywords


allyl trichloroacetimidates; aminocarbohydrates; 1,6-anhydromannose; levoglucosenone; oxazoline

Full Text: PDF (Russian) Supplementary File(s): Supporting information (1MB)


 

 

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv