Synthesis of anomeric sulfonamides and their behaviour under radical-mediated bromination conditions

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Abstract

O-Peracetylated methyl 3-(d-glycopyranosylthio)propanoates of β-d-gluco, and α- and β-d-galacto configurations were oxidized to the corresponding S,S-dioxides (sulfones) by Oxone® or MCPBA. Oxidation of the β-d-gluco derivative with H2O2/Na2WO4 gave the corresponding S-oxide (sulfoxide). DBU-induced elimination of methyl acrylate from the β-d-gluco and β-d-galacto configured S,S-dioxides (sulfones) gave O-peracetylated β-d-glycopyranosyl-1-C-sulfinates which, on treatment with H2NOSO3H, furnished the corresponding β-d-glycopyranosyl-1-C-sulfonamides. Radical-mediated bromination of the protected methyl 3-(β-d-glycopyranosylthio)propanoate S,S-dioxides gave mixtures of 1-C- and 5-C-bromoglycosyl compounds. Similar brominations of the O-peracetylated β-d-glycopyranosyl-1-C-sulfonamides resulted in the formation of α-d-glycopyranosyl bromides and 1-C- and 5-C-bromoglycosyl sulfonamides. A rationale for these observations was proposed. Methyl 3-(β-d-glucopyranosylthio)propanoate, its S,S-dioxide, and β-d-glucopyranosyl-1-C-sulfonamide proved inefficient when tested as inhibitors of rabbit muscle glycogen phosphorylase b.

Original languageEnglish
Pages (from-to)269-277
Number of pages9
JournalCarbohydrate Research
Volume344
Issue number3
DOIs
Publication statusPublished - Feb 17 2009

Keywords

  • Bromination
  • Glycopyranosyl
  • Radical
  • Sulfonamide

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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