Synthesis of ν-triazole derivatives from anomeric sugar diazides

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Abstract

Staudinger reaction of acetylated glycopyranosylidene 1,1-diazides led to resonance-stabilized iminophosphoranes (phosphinimines) of 6,7-dihydro[3,4-d]-1,2,3-triazole. This unprecedented transformation involves β-elimination of acetic acid and cycloaddition of azide anion to the resulting C-2 double bond. Transformation of the new fused heterocyclic iminophosphoranes on treatment with aqueous ethanolic ammonia gives carboxamidine derivatives of ν-triazole bearing a chiral trihydroxypropyl side-chain. Crystal structure of 5-(d-erythro-1',2',3'-trihydroxypropyl)-1,2,3-triazole-4-carboxamidine was established by X-ray crystallography. Copyright (C) 1999 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)112-120
Number of pages9
JournalCarbohydrate Research
Volume316
Issue number1-4
DOIs
Publication statusPublished - Mar 15 1999

Keywords

  • Azido sugars
  • Glycopyranosylidene 1,1-diazides
  • Iminophosphoranes (phosphinimines)
  • Pyrano[3,4-D]-1,2,3-triazole
  • Staudinger reaction
  • X-ray structure

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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