TY - JOUR
T1 - A New Approach to Some 1,6-Dideoxy 1,6-Epithio Sugars
AU - Driguez, H.
AU - Mcauliffe, J.C.
AU - Stick, Robert
AU - Tilbrook, Matthew
AU - Williams, S.J.
PY - 1996
Y1 - 1996
N2 - The treatment of hexopyranosyl bromides, also activated at C 6 (Br, OTs, OMs), with H2S/HCONMe(2) 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-beta-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.
AB - The treatment of hexopyranosyl bromides, also activated at C 6 (Br, OTs, OMs), with H2S/HCONMe(2) 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-beta-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.
U2 - 10.1071/CH9960343
DO - 10.1071/CH9960343
M3 - Article
SN - 0004-9425
VL - 49
SP - 343
EP - 348
JO - Australian Journal of Chemistry: an international journal for chemical science
JF - Australian Journal of Chemistry: an international journal for chemical science
ER -