Aza-Wittig reaction of sugar isothiocyanates and sugar iminophosphoranes: An easy entry to unsymmetrical sugar carbodiimides

José M. García Fernández, Carmen Ortiz Mellet, Víctor M. Díaz Pérez, J. Fuentes, József Kovács, István Pintér

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Abstract

Aldohexose derivatives possessing a triphenylphosphoranylideneamino substituent at the primary (C-6) position exhibit an increased reactivity towards the aza-Wittig condensation with isothiocyanates as compared with glycosyl phosphinimines. The reaction is particularly fast and efficient in the case of glycosyl isothiocyanates and has been exploited in the preparation of (1→6)-linked pseudooligosaccharides incorporating carbodiimide bridges. These compounds are excellent starting materials for the preparation of sugar ureas, thioureas and guanidines by reaction with the appropriate nucleophile.

Original languageEnglish
Pages (from-to)4161-4164
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number23
DOIs
Publication statusPublished - Jun 9 1997

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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