The Synthesis of Various 1,6-Disulfide-Bridged d-Hexopyranoses^*

Ethan D. Goddard-Borger ^A and Robert V. Stick <sup>A B

A</sup> 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

1,6-Disulfide-bridged derivatives have been prepared for d-gluco-, d-manno-, d-allo-, d-galacto-, and d-talo-pyranose, in the main by the nucleophilic attack of a C6 thiolate onto an anomeric thiosulfonate. The d-gluco disulfide, ‘angyalosan’, was successfully oxidized to a single thiosulfinate.

Australian Journal of Chemistry 58(3) 188–198    doi:10.1071/CH04277
Submitted: 21 November 2004    Accepted: 7 February 2005    Published: 15 March 2005






^* In celebration of the 90th birthday of Stephen J. Angyal.

^* The spectrum was obtained at 233 K and two sets of resonances were observed, assigned to two conformers, a and b. The ¹H and ¹³C resonances for each conformer were assigned using COSY, HSQC, and HMBC two-dimensional spectra.

^† The ¹H and ¹³C NMR spectra [300 MHz, (CD₃)₂SO] were uninterpretable at 293 K.

^§ [1S,4S,5S,6S,7R]-5,6,7-Triacetoxy-8-oxa-2-thiabicyclo[3.2.1]octane.

^¶ [1S,4S,5S,6S,7R]-5,6,7-Triacetoxy-8-oxa-2-selenabicyclo[3.2.1]octane.