
%0 Journal Article
%A Driguez, H 
%A Mcauliffe, JC 
%A Stick, RV 
%A Tilbrook, DMG 
%A Williams, SJ 
%T A New Approach to Some 1,6-Dideoxy 1,6-Epithio Sugars
%J Australian Journal of Chemistry
%D 1996/03/01
%V 49
%N 3
%P 343-348
%K 
%R https://doi.org/10.1071/CH9960343
%U https://www.publish.csiro.au/paper/CH9960343 
%X The treatment of hexopyranosyl bromides, also activated at C6 (Br, OTs, OMs), with H2S/HCONMe2 under basic conditions gives rise to 1,6-dideoxy 1,6-epithio sugars. One such sugar has been further transformed into the synthetically useful 3,4-anhydro-1,6-dideoxy-1,6-epithio-&#946;-D-galactose. The treatment of this epoxide with sodium azide and with cyclohexylamine is described. An analogous treatment of one doubly activated hexopyranosyl bromide with sodium hydrogen selenide has led to a novel 1,6-dideoxy 1,6-episeleno sugar which displayed interesting n.m.r. spectra. Finally, in an attempt to prepare 1,6-dideoxy 1,6-epidithio sugars, a tetraalkylammonium tetrathiomolybdate reagent was found to be the reagent of choice for converting doubly activated hexopyranosyl bromides into 1,6-dideoxy 1,6-epithio sugars. 
