Synthesis of Deoxy Sugars. Deoxygenation by Treatment with N,N'-Thiocarbonyldiimidazole/Tri-n-butylstannane

Article abstract of DOI:10.1021/jo00337a004

Protected sugars containing a free hydroxyl group have been deoxygenated by conversion to the O-(imidazolylthiocarbonyl) derivative with N,N'-thiocarbonyldiimidazole followed by treatment with tri-n-butylstannane.This reaction sequence offers a mild, high-yield procedure for the deoxygenation of hexose derivatives with a hindered secondary hydroxyl group at C-3 or C-4.The primary 6-O-(imidazolylthiocarbonyl) compound obtained from 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose reacts with tri-n-butylstannane to give a mixture of the 6-deoxy sugar (31percent) and starting alcohol (57percent).