CSIRO PUBLISHING - Australian Journal of Chemistry

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 ^A

^A 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

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.

Australian Journal of Chemistry 58(3) 199–205 doi:10.1071/CH04291
Submitted: 7 December 2004 Accepted: 7 February 2005 Published: 15 March 2005