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| Titel: |
Radical-Mediated Halogenations of Anomerically N-Substituted Glucopyranosyl Derivatives |
| Auteur: |
Praly, J. -P. Somsak, L. Mahmoud, S. H. Kharraf, Z. El Descotes, G. Farkas, I. |
| Verschenen in: |
Journal of carbohydrate chemistry |
| Paginering: | Jaargang 11 (1992) nr. 3 pagina's 201-216 |
| Jaar: |
1992-04-01 |
| Inhoud: |
Reactions of acetylated N-aryl-D-glucosylamines with N-bromosuccinimide-benzoyl peroxide or with sulfuryl chloride-azoisobutyronitrile gave aromatic halo derivatives. The corresponding N-acetylated compounds were mostly inert towards halogenation. Bromination of acetylated cellobiosylpiperidine resulted in the formation of acetobromocellobiose, while the acetylated 2,6,8-trichloro-9-(β-D-glucopyranosyl)-purine was transformed into its 5'-bromo derivative. In contrast, peracetylated glucopyranosyl isothiocyanate or azides, when treated by N-bromosuccinimide under free-radical conditions, essentially undergo an initial homolysis of the anomeric C-H bond which is faster for β-anomers. This initiates a new, simple and efficient free-radical transformation of such sugar azides into an unprecedented brornimino lactone (92% isolated yield). |
| Uitgever: |
Taylor & Francis |
| Bronbestand: |
Elektronische Wetenschappelijke Tijdschriften |
Details van artikel 124 van 252 gevonden artikelen
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