
TY  - JOUR
A1  - Patroni, JJ 
A1  - Stick, RV 
A1  - Engelhardt, LM 
A1  - White, AH 
T1  - The Deoxygenation of Some Carbohydrate Diols Via the Derived Cyclic Thiocarbonate
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1986
VL  - 39
IS  - 4
SP  - 699
EP  - 711
KW  - 
UR  - https://doi.org/10.1071/CH9860699 
N2  - The treatment of methyl 2,6-di-O-methyl-3,4-O-thiocarbonyl-&#946;-D-galactoside with methyl iodide gives mainly the 3-deoxy-3-iodo-D-guloside , whereas the &#945;- anomer of the above and methyl 2-O-methyl-3,4- O- thiocarbonyl-&#946;-L-arabinoside give mainly the 4-deoxy-4-iodo-D- glycosides. An explanation is given for these and some previously reported results. As well, two of the above cyclic thiocarbonates (&#946;-D-galacto and &#946;-L- arabino), together with two cyclic thiocarbonates derived from methyl &#945;-D- mannopyranoside, when treated with tributyltin hydride, gave mixtures (nearly 1:1) of products resulting from deoxygenation . Single-crystal X-ray diffraction structure determination of the &#946;-D- galacto and the &#946;-L- arabino cyclic thiocarbonates showed both pyranose rings to be in the 4C1 conformation. 
ER  -

