The Photohydration of N-Glycosylpyridinium Salts and of Related Pyridinium N,O-Acetals

✍ Scribed by Fabrice Glarner; Bilge Acar; Isabelle Etter; Teresa Damiano; Ersin A. Acar; Gérald Bernardinelli; Ulrich Burger

• Book ID: 104202741
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 145 KB
• Volume: 56
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(00)00357-4

✦ Synopsis

AbstractÐThe photolysis of N-MEM-pyridinium chloride (1e) in alkaline H 2 O gave N-MEM-6-azabicyclo[3.1.0]hexenol (2e). With benzoic acid in CHCl 3 , this bridged aziridine gave a complex aminal 7 reminiscent by its C 2 symmetry of Tro Èger's base. Photolysis of a-d-glucopyranosyl pyridinium chloride (a-12) gave a 1:1 mixture of the corresponding a-d-glucopyranosyl aziridines (a-13/a-14), which were separated, after peracetylation, by crystallisation. The absolute con®guration of one of the bridged aziridines (a-16) was established by X-ray analysis.