Glycosyl iodides are highly efficient donors under neutral conditions

Michael J. Hadd, Jacquelyn Gervay-Hague

Research output: Contribution to journalArticle

100 Scopus citations

Abstract

Glycosyl iodides have been prepared and subjected to glycosylation under neutral conditions. The reactions are highly efficient, giving α glycosides even with sterically demanding glycosyl acceptors. Glucosyl iodides react with allyl alcohol slowest and require refluxing conditions. Galactosyl iodides are intermediate in reactivity, providing the allyl glycoside in 3 h at room temperature, whereas glycosylation of fucosyl iodides occurs in less than 1 h under similar conditions. The scope and limitations of the reactions were demonstrated with a variety of acceptors, including an anomeric hydroxyl group, to give trehalose analogs. β-Selective glycosylation of glucosyl iodides, in the absence of C-2 participation, could be achieved by simply changing the solvent from benzene to acetonitrile. Copyright (C) 1999 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)61-69
Number of pages9
JournalCarbohydrate Research
Volume320
Issue number1-2
DOIs
StatePublished - Jul 20 1999
Externally publishedYes

Keywords

  • Glycosyl bromide
  • Glycosyl iodide
  • Halide-catalyzed anomerization
  • In situ anomerization
  • Trehalose analogs
  • α-Glycosylation

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

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