The conformation of some 1,6-disulfide-bridged D-hexopyranoses

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] nonane2-oxide. © CSIRO 2005.