Transformation of aldose formazans. Novel synthesis of 2-acetamido-2- deoxypentonolactones and a new pent-2-enose formazan

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3 Citations (Scopus)

Abstract

2-Acetamido-2-deoxypentonolactones were synthesized from per-O-acetylated formazans of d-ribose, d- and l-arabinose, respectively. In dimethyl sulfoxide, a novel spontaneous transformation of the per-O-acetyl-pentose formazans into new 3,4,5-tri-O-acetyl-pent-2-enose formazans has been recognized. Additional examples for the occurrence of the isomerism between pseudo-aromatic chelate and open phenylazo-phenylhydrazone system were demonstrated by 1H NMR spectroscopy in both the unprotected pentose formazans and 3,4,5-tri-O-acetyl- pent-2-enose formazans. Computational calculations supported higher stability of the ring form.

Original languageEnglish
Pages (from-to)1534-1540
Number of pages7
JournalCarbohydrate Research
Volume346
Issue number12
DOIs
Publication statusPublished - Sep 6 2011

Keywords

  • 2-Acetamido-2-deoxy- pentonolactones
  • 2-Acetamido-2-deoxy-pentose formazans
  • Acetylated pent-2-enose formazans
  • Isomerism of the formazan ring
  • Per-O-acetyl-pentose formazans
  • Regiospecific introduction of amino function

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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