Radical-mediated halogenations of anomerically n-substituted glucopyranosyl derivatives

J. P. Praly, Z. E. Kharraf, G. Descotes, L. Somsák, S. H. Mahmoud, I. Farkasb

Research output: Article

7 Citations (Scopus)

Abstract

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-(p-D-ghicopyranosyl)-purine was transformed into its 5‘-bromo derivative. In contrast, peracetylated glucopyranosyl isothiocyanate or azides, when treated by W-bromosuccinimide under free-radical conditions, essentially undergo an initial homolysis of the anomeric C-H bond which is faster for p-anomers. This initiates a new, simple and efficient free-radical transformation of such sugar azides into an unprecedented bromimino lactone (92 % isolated yield).

Original languageEnglish
Pages (from-to)201-216
Number of pages16
JournalJournal of Carbohydrate Chemistry
Volume11
Issue number3
DOIs
Publication statusPublished - ápr. 1 1992

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Halogenation
Bromosuccinimide
Azides
Free Radicals
Benzoyl Peroxide
Derivatives
Lactones
Sugars
Chlorides

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

Cite this

Radical-mediated halogenations of anomerically n-substituted glucopyranosyl derivatives. / Praly, J. P.; Kharraf, Z. E.; Descotes, G.; Somsák, L.; Mahmoud, S. H.; Farkasb, I.

In: Journal of Carbohydrate Chemistry, Vol. 11, No. 3, 01.04.1992, p. 201-216.

Research output: Article

Praly, J. P. ; Kharraf, Z. E. ; Descotes, G. ; Somsák, L. ; Mahmoud, S. H. ; Farkasb, I. / Radical-mediated halogenations of anomerically n-substituted glucopyranosyl derivatives. In: Journal of Carbohydrate Chemistry. 1992 ; Vol. 11, No. 3. pp. 201-216.
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AU - Mahmoud, S. H.

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AB - 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-(p-D-ghicopyranosyl)-purine was transformed into its 5‘-bromo derivative. In contrast, peracetylated glucopyranosyl isothiocyanate or azides, when treated by W-bromosuccinimide under free-radical conditions, essentially undergo an initial homolysis of the anomeric C-H bond which is faster for p-anomers. This initiates a new, simple and efficient free-radical transformation of such sugar azides into an unprecedented bromimino lactone (92 % isolated yield).

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