The Journal of Organic Chemistry

Synthesis of deoxyhalogeno sugars. Reaction of halide ions with 1, 2, 3, 4-tetra-O-acetyl-6-O-[(trifluoromethyl) sulfonyl]-. beta.-D-glucopyranose

MG Ambrose, RW Binkley

文献索引：Ambrose, Michael G.; Binkley, Roger W. Journal of Organic Chemistry, 1983 , vol. 48, # 5 p. 674 - 677

全文：HTML全文

被引用次数: 39

摘要

The reaction of bromide, chloride, and iodide ions with 1, 2, 3, 4-tetra-0-acetyl-6-0- [(trifluoromethyl)-sulfonyl]-~-~-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 ...