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

José Manuel García Fernández, Carmen Ortiz Mellet, Víctor Manuel Díaz Pérez, José Fuentes, J. Kovács, I. Pintér

Research output: Article

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

Fingerprint

Isothiocyanates
Carbodiimides
Sugars
Trisaccharides
Azides
Derivatives
Kinetics
3'-azido-2',3'-dideoxythymidine 5'-H-phoshonate
coupling sugar
triphenylphosphine

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Synthesis of (1 → 6)-carbodiimide-tethered pseudooligosaccharides via aza-Wittig reaction. / García Fernández, José Manuel; Ortiz Mellet, Carmen; Díaz Pérez, Víctor Manuel; Fuentes, José; Kovács, J.; Pintér, I.

In: Carbohydrate Research, Vol. 304, No. 3-4, 28.11.1997, p. 261-270.

Research output: Article

García Fernández, José Manuel ; Ortiz Mellet, Carmen ; Díaz Pérez, Víctor Manuel ; Fuentes, José ; Kovács, J. ; Pintér, I. / Synthesis of (1 → 6)-carbodiimide-tethered pseudooligosaccharides via aza-Wittig reaction. In: Carbohydrate Research. 1997 ; Vol. 304, No. 3-4. pp. 261-270.
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AU - García Fernández, José Manuel

AU - Ortiz Mellet, Carmen

AU - Díaz Pérez, Víctor Manuel

AU - Fuentes, José

AU - Kovács, J.

AU - Pintér, I.

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KW - aza-Wittig reaction

KW - Pseudoligosaccharride

KW - Sugar carbodiimide

KW - Sugar iminophosphoranes

KW - Sugar isothiocyanate

KW - Sugar phosphazides

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