An easy access to anomeric glycosyl amides and imines (Schiff bases) via transformation of glycopyranosyl trimethylphosphinimides

László Kovács, Erzsébet Osz, Valéria Domokos, Wolfgang Holzer, Zoltán Györgydeák

Research output: Contribution to journalArticle

52 Citations (Scopus)

Abstract

The preparation and application of anomeric glycosyl phosphinimides in preparative synthesis were studied. Starting from the appropriate glycosyl azides and trialkyl or triaryl phosphines, the corresponding phosphinimides were obtained by modified Staudinger reactions. The latter compounds were readily converted into 1-N-acyl-gluco- and galactopyranosyl amines with high yields by applying activated acid derivatives or simple carboxylic acids. 1-N-Alkylidene- or arylidenephosphinimines (Schiff bases) were obtained by means of aza-Wittig reactions using aliphatic or aromatic aldehydes, respectively.

Original languageEnglish
Pages (from-to)4609-4621
Number of pages13
JournalTetrahedron
Volume57
Issue number21
DOIs
Publication statusPublished - May 21 2001

Keywords

  • Glycosyl amides
  • Glycosyl imides
  • Glycosyl imines
  • Staudinger reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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