Convenient syntheses of symmetrical and unsymmetrical glycosyl carbodiimides and N,N-bis(glycosyl)cyanamides

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Abstract

Reaction of glycosyl trimethylphosphinimides with carbon disulfide under mild conditions (room temperature, short reaction time) leads to symmetrical glycosyl carbodiimides. Addition of bis(trimethylsilyl)carbodiimide to peracetylated aldoses under the influence of SnCl4 afforded N,N-bis(glycosyl)cyanamides for the first time. Readily accessible unsymmetrical N,N′-bis(glycosyl)thioureas can be desulfurated and transformed into the corresponding carbodiimides using HgO in CHCl3/water at room temperature.

Original languageEnglish
Pages (from-to)1171-1178
Number of pages8
JournalCarbohydrate Research
Volume337
Issue number13
DOIs
Publication statusPublished - Jul 16 2002

Keywords

  • Glycosyl azides
  • Glycosyl carbodiimides
  • Glycosyl cyanamides
  • Staudinger reaction

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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