Synthesis of halogenated-4-nitrophenyl 2-deoxy-2-halogeno-pyranosides via n-halogenosuccinimide activated glucal

Chieri Inoue, Yumi Okamoto, Christopher J. Vavricka, Hiromasa Kiyota, Minoru Izumi

Research output: Contribution to journalArticle

Abstract

Reaction of 3,4,6-tri-O-acetyl-D-glucal with silver 4-nitrophenolate in the presence of N-iodosuccinimide and N-bromosuccinimide produced (2,6-dihalo-4-nitro)phenyl 2-halo-2-deoxy--D-glycopyranosides. Although bromination and iodination of the 4-nitrophenyl group could not be avoided, the resulting (2,6-dihalo-4-nitro)phenylated compounds can be used as substrates or covalent glycosidase inhibitors after deprotection. The stereoselectivity and regioselectivity of the halogenation reactions are described.

Original languageEnglish
Pages (from-to)85-87
Number of pages3
JournalNatural product communications
Volume13
Issue number1
DOIs
Publication statusPublished - Jan 1 2018

Keywords

  • 2-Deoxy sugar
  • 2-Deoxy-2-halogeno-pyranoside
  • Glucal
  • N-Halogenosuccinimide
  • Silver 4-nitrophenolate

ASJC Scopus subject areas

  • Pharmacology
  • Plant Science
  • Drug Discovery
  • Complementary and alternative medicine

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