A conformational study of dioxolane-type acetals of some carbohydrate derivatives by N.M.R. spectroscopy

János Harangi, A. Lipták, Zoltán Szurmai, Pál Nánási

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The conformation of the methylene, isopropylidene, benzylidene, and 1-phenylethylidene acetals of some rhamnopyranoside and arabinopyranoside derivatives has been investigated by n.m.r. spectroscopy. In each series, the pyranoside ring adopts a distorted chair conformation. For the benzylidene acetals, the pyranoside ring is more distorted in the endo-phenyl isomers, and these isomers are compared to the methylene and isopropylidene acetals. For the 1,3-dioxolane ring, only the coupling constant of the acetal carbon atom with the axial bridgehead proton is measurable; for the benzylidene acetals, it is larger in the exo-phenyl isomer. For the other types of acetals, the coupling constant depends on the nature of the endo substituent at the acetal carbon atom. If it is bulky, the coupling constant and the conformation of the dioxolane ring are similar to those of the corresponding endo-phenyl benzylidene derivative.

Original languageEnglish
Pages (from-to)241-248
Number of pages8
JournalCarbohydrate Research
Volume136
Issue numberC
DOIs
Publication statusPublished - Feb 28 1985

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Acetals
Nuclear magnetic resonance spectroscopy
Magnetic Resonance Spectroscopy
Carbohydrates
Derivatives
Isomers
Conformations
Carbon
Atoms
formal glycol
Protons
Spectrum Analysis
Spectroscopy

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

A conformational study of dioxolane-type acetals of some carbohydrate derivatives by N.M.R. spectroscopy. / Harangi, János; Lipták, A.; Szurmai, Zoltán; Nánási, Pál.

In: Carbohydrate Research, Vol. 136, No. C, 28.02.1985, p. 241-248.

Research output: Contribution to journalArticle

Harangi, János ; Lipták, A. ; Szurmai, Zoltán ; Nánási, Pál. / A conformational study of dioxolane-type acetals of some carbohydrate derivatives by N.M.R. spectroscopy. In: Carbohydrate Research. 1985 ; Vol. 136, No. C. pp. 241-248.
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