Synthesis of Deoxyhalogenosugars. Reaction of Halide Ions with 1,2,3,4-Tetra-O-acetyl-6-O--β-D-glucopyranose

Article abstract of DOI:10.1021/jo00153a011

The reaction of bromide, chloride, and iodide ions with 1,2,3,4-tetra-O-acetyl-6-O-<(trifluoromethyl)-sulfonyl>-β-D-glucopyranose under the proper conditions gives excellent yields of the corresponding deoxyhalogeno sugars.Deoxyiodo sugars form readily under all conditions studied.Difficulties with displacements by bromide and chloride are encountered but can be overcome by appropriate modification of reaction conditions.Displacement with fluoride ion is difficult and produces only a low yield of the expected fluorinated carbohydrate.