Synthesis of (1 → 6)-carbodiimide-tethered pseudooligosaccharides via aza-Wittig reaction

José Manuel García Fernández, Carmen Ortiz Mellet, Víctor Manuel Díaz Pérez, José Fuentes, József Kovács, István Pintér

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26 Citations (Scopus)

Abstract

The synthesis of unsymmetrical sugar carbodiimides through aza-Wittig coupling of sugar derived iminophosphoranes and isothiocyanates is reported. The reaction is particularly fast and efficient in the case of phosphoranylide derivatives of 6-azido-6-deoxysugars and glycosyl isothiocyanates, and has been exploited in the one-pot preparation of (1 → 6)-linked pseudodi- and trisaccharides incorporating carbodiimide bridges as convenient precursors for the corresponding ureido, thioureido, and guanidino derivatives. Kinetic considerations suggest that sugar phosphazides, formed in the early stages of the Staudinger reaction of triphenylphosphine and sugar azides, are the reactive intermediates.

Original languageEnglish
Pages (from-to)261-270
Number of pages10
JournalCarbohydrate Research
Volume304
Issue number3-4
DOIs
Publication statusPublished - Nov 28 1997

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Keywords

  • Pseudoligosaccharride
  • Sugar carbodiimide
  • Sugar iminophosphoranes
  • Sugar isothiocyanate
  • Sugar phosphazides
  • aza-Wittig reaction

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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