
TY  - JOUR
A1  - Driguez, H 
A1  - Mcauliffe, JC 
A1  - Stick, RV 
A1  - Tilbrook, DMG 
A1  - Williams, SJ 
T1  - A New Approach to Some 1,6-Dideoxy 1,6-Epithio Sugars
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1996
VL  - 49
IS  - 3
SP  - 343
EP  - 348
KW  - 
UR  - https://doi.org/10.1071/CH9960343 
N2  - 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. 
ER  -

