The Conformation of Some 1,6-Disulfide-Bridged d-Hexopyranoses
Ethan D. Goddard-Borger A , Brian W. Skelton A , Robert V. Stick A B and Allan H. White AA Chemistry M313, School of Biomedical and Chemical Sciences, University of Western Australia, Crawley WA 6009, Australia.
B Corresponding author. Email: rvs@chem.uwa.edu.au
Australian Journal of Chemistry 58(3) 199-205 https://doi.org/10.1071/CH04291
Submitted: 7 December 2004 Accepted: 7 February 2005 Published: 15 March 2005
Abstract
The use of 1H NMR spectroscopy, in tandem with X-ray crystallography, has cast light on the conformation of the 1,6-disulfide-bridged derivatives of d-gluco-, d-manno-, d-allo-, d-galacto-, and d-talo-pyranose. A similar investigation was performed on the thiosulfinate derived from the d-gluco disulfide. Single-crystal X-ray structure determinations are reported for (1S,5S,6S,7S,8R)-6,7,8-tribenzoyloxy-9-oxa-2,3-dithiabicyclo[3.3.1]nonane, (1S,5S,6S,7R,8R)-6,7,8-tribenzoyloxy-9-oxa-2,3-dithiabicyclo[3.3.1]nonane, and (1S,2S,5S,6S,7S,8R)-6,7,8-triacetoxy-9-oxa-2,3-dithiabicyclo[3.3.1]nonane 2-oxide.
Acknowledgments
E.D.G.-B. is grateful for financial assistance provided by a Raoul Robellaz Kahan Scholarship.
[1]
E. D. Goddard-Borger,
R. V. Stick,
Aust. J. Chem. 2005, 58, 188.
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* Note that the numbering no longer follows carbohydrate guidelines but is consistent with IUPAC bicyclic nomenclature.
† The 1H and 13C NMR spectra (300 MHz) were uninterpretable at 293 K.
