Synthesis and chiroptical properties of (naphthyl)ethylidene ketals of carbohydrates in solution and solid state

Gábor Kerti, Tibor Kurtán, Anikó Borbás, Zoltán B. Szabó, András Lipták, László Szilágyi, Zita Illyés-Tünde, Attila Bényei, Sándor Antus, Masayuki Watanabe, Ettore Castiglioni, Gennaro Pescitelli, Piero Salvadori

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21 Citations (Scopus)

Abstract

1,3-Dioxolane- and dioxane-type (1- and 2-naphthyl)ethylidene ketals of p-methoxyphenyl α-l-rhamnopyranoside and β-d-glucopyranoside were prepared and their stereochemistry studied by solution and solid-state circular dichroism, X-ray diffraction, and coupled-oscillator CD calculations on the solid-state and MMFF-calculated geometries. Intermolecular exciton-coupled interactions between the nearby aromatic chromophores in the solid state and different conformers in solution and solid state could be identified as the main reason for the difference between solution and solid-state CDs.

Original languageEnglish
Pages (from-to)1676-1688
Number of pages13
JournalTetrahedron
Volume64
Issue number8
DOIs
Publication statusPublished - Feb 18 2008

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Keywords

  • 1- and 2-Naphthyl chromophores
  • Intra- and intermolecular exciton-coupled interactions
  • Solid-state CD

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Kerti, G., Kurtán, T., Borbás, A., Szabó, Z. B., Lipták, A., Szilágyi, L., Illyés-Tünde, Z., Bényei, A., Antus, S., Watanabe, M., Castiglioni, E., Pescitelli, G., & Salvadori, P. (2008). Synthesis and chiroptical properties of (naphthyl)ethylidene ketals of carbohydrates in solution and solid state. Tetrahedron, 64(8), 1676-1688. https://doi.org/10.1016/j.tet.2007.12.011