Circular Dichroism of 1,3-Dioxane-Type (2′-Naphthyl)Methylene Acetals of Glycosides

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Abstract

The CD spectra are reported for a series of 1,3-dioxane-type 4,6-O-(2′-naphthyl) methylene acetals of carbohydrates with and without interacting aromatic protective groups on the C-1, C-2, and C-3 hydroxy groups. In the absence of interacting chromophores, the signs of the 1B transitions are not sensitive to the configuration of C-4, while the signs of the weak 1La bands are opposite in the galacto and gluco derivatives. The equatorial parallel conformation is found to be the preferred conformation of the 2-naphthyl group in the solid state by X-ray diffraction. The intense 1Ba and 1Bb transitions of the naphthalene chromophore allowed a safe configurational assignment by exciton coupled interaction with the aromatic protective groups in para-methoxyphenyl-β-D-glycosides. The origin of the observed CEs were deduced and the additivity of the interactions was studied. The direction of the hydrogenolytic cleavage of 4,6-O-(2′-naphthyl)methylene acetal of carbohydrates could also be detected by the 1Bb transition of the 2-naphthyl chromophore.

Original languageEnglish
Pages (from-to)244-250
Number of pages7
JournalChirality
Volume16
Issue number4
DOIs
Publication statusPublished - Apr 27 2004

Keywords

  • 2-naphthyl chromophore
  • Acetal
  • Circular dichroism
  • Exciton coupled interaction
  • Sector rule

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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