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

Article Article scientifique Article The Photohydration of N-Glycosylpyridinium Salts and of Related Pyridinium N,O-Acetals eng 2000 author Glarner Fabrice Jean 83193 author Acar Bilge 506575 author Etter Isabelle 83864 author Damiano Maria Teresa 503872 author Acar Ersin Ali author Bernardinelli Gérald Hugues 24765 author Burger Ulrich 25497 4311-4316 10.1016/S0040-4020(00)00357-4 0040-4020 https://linkinghub.elsevier.com/retrieve/pii/S0040402000003574 The photolysis of N-MEM-pyridinium chloride (1e) in alkaline H2O gave N-MEM-6-azabicyclo[3.1.0]hexenol (2e). With benzoic acid in CHCl3, this bridged aziridine gave a complex aminal 7 reminiscent by its C2 symmetry of Tröger's base. Photolysis of α-d-glucopyranosyl pyridinium chloride (α-12) gave a 1:1 mixture of the corresponding α-d-glucopyranosyl aziridines (α-13/α-14), which were separated, after peracetylation, by crystallisation. The absolute configuration of one of the bridged aziridines (α-16) was established by X-ray analysis. Bridged aziridines Tröger's base Aminocyclopentitols Glucosylamines Dewey 540 Swiss National Science Foundation 20-52905.97 CH 36 Département de chimie organique 141 false Tetrahedron 56 25 0ef435b8-42a6-41b9-beda-b9b212d93713 Article (Published version) Restricted 1-s2.0-S0040402000003574-main.pdf 148649 application/pdf restrictedAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

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The Photohydration of N-Glycosylpyridinium Salts and of Related Pyridinium N,O-Acetals	Tetrahedron			2000	295	0

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Etter, Isabelle