Summary
Infrared spectra of a number of acetylated and benzoylated glycopyranosyl fluorides have been taken. It has been observed that, with a single exception, compounds in which the fluorine atom is axially bound absorb in the region 748–802 cm−1 whereas compounds with an equatorially bound fluorine atom show no absorption in this region. The infrared spectra may be used to assign the anomeric configuration of glycopyranosyl fluorides if their conformation is known.
Zusammenfassung
Die IR-Spektren einiger acetylierter und benzoylierter Glykopyranosylfluoride wurden aufgenommen. Dabei wurde beobachtet, daß alle Verbindungen mit axial gebundenem Fluor mit einer einzigen Ausnahme in dem Gebiet 748 bis 802 cm−1 absorbieren, während Verbindungen mit äquatorial gebundenem Fluor in diesem Gebiet keine Absorption zeigen. Die IR-Spektren können daher zur Feststellung der anomeren Konfiguration solcher Verbindungen dienen, soferne deren Konformation bekannt ist.
Résumé
On a enregistré le spectre infrarouge d'un certain nombre de fluorures de glycopyranosyles acétylés et benzoylés. On a observé, à une seule exception près, que les composés dans lesquels l'atome de fluor est lié axialement absorbent dans la région 748–820 cm−1, tandis que ceux où le fluor est lié équatorialement ne montrent pas d'absorption dans cette région. On peut utiliser les spectres d'absorption infrarouge pour déterminer la configuration anomère des fluorures de glycopyranosyle si leur conformation est connue.
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Dedicated to Prof. Dr. Ing.M. Jureček on the occasion of his 60th birthday.
The authors are indebted to cand. pharmI. Krogh Andersen for the infrared spectra. Microanalyses were made by Mr.Preben Hansen.
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Lundt, I., Pedersen, C. Infrared spectra of acetylated and benzoylated glycopyranosyl fluorides. Mikrochim Acta 54, 126–132 (1966). https://doi.org/10.1007/BF01217441
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DOI: https://doi.org/10.1007/BF01217441