Crystal structures, circular dichroism spectra and absolute configurations of some l-ascorbic acid derivatives

Chiral 2,3-O,O-dibenzyl ethers of l-ascorbic acid with 4-(5,6-epoxy)- (4) and 6-O-tosyl- (8) functional groups were studied by X-ray crystallography and circular dichroism (CD) spectroscopy. The stereostructure of 2,3-O,O-dibenzyl-5,6-isopropylidene-l-ascorbic acid (6) and 8 was determined by X-ray...

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Bibliographic Details
Published in:Journal of molecular structure 2004-01, Vol.687 (1-3), p.101-106
Main Authors: Wittine, Karlo, Gazivoda, Tatjana, Markuš, Marko, Mrvoš-Sermek, Draginja, Hergold-Brundić, Antonija, Cetina, Mario, Žiher, Dinko, Gabelica, Vesna, Mintas, Mladen, Raić-Malić, Silvana
Format: Article
Language:English
Subjects:
Circular dichroism spectroscopy
Cotton effect
l-Ascorbic acid derivatives
Single crystal X-ray diffraction
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Summary:Chiral 2,3-O,O-dibenzyl ethers of l-ascorbic acid with 4-(5,6-epoxy)- (4) and 6-O-tosyl- (8) functional groups were studied by X-ray crystallography and circular dichroism (CD) spectroscopy. The stereostructure of 2,3-O,O-dibenzyl-5,6-isopropylidene-l-ascorbic acid (6) and 8 was determined by X-ray crystal structure analysis. Comparison of the CD-spectra of 4 and 8 with the CD-spectra of their synthetic precursors (2–3, 5–7) and l-ascorbic acid (1) itself, as well as crystal structures of 6 and 8 permitted to deduce the absolute configuration of 4. Thus, the chiral atoms C-4 and C-5 in 4 have R and S configurations, which is consistent with the configuration of 1.
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2003.09.019