Scientific article
English

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

Published inTetrahedron, vol. 56, no. 25, p. 4311-4316
Publication date2000
Abstract

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.

Keywords
  • Bridged aziridines
  • Tröger's base
  • Aminocyclopentitols
  • Glucosylamines
Funding
  • Swiss National Science Foundation - 20-52905.97
Citation (ISO format)
GLARNER, Fabrice Jean et al. The Photohydration of N-Glycosylpyridinium Salts and of Related Pyridinium N,O-Acetals. In: Tetrahedron, 2000, vol. 56, n° 25, p. 4311–4316. doi: 10.1016/S0040-4020(00)00357-4
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Article (Published version)
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Identifiers
Journal ISSN0040-4020
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