79233-82-2Relevant academic research and scientific papers
Synthesis of Deoxy Sugars. Deoxygenation by Treatment with N,N'-Thiocarbonyldiimidazole/Tri-n-butylstannane
Rasmussen, James R.,Slinger, Cheryl J.,Kordish, Rebecca J.,Newman-Evans, Dana D.
, p. 4843 - 4846 (2007/10/02)
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).
