M. L. Shul'man, A. Khorlin
Mar 1, 1973
Citations
0
Influential Citations
17
Citations
Journal
Carbohydrate Research
Abstract
Abstract Benzyl 2-acetamido-2-deoxy-α- D -glucopyranoside was mesylated selectively at position 6. Benzylation of the resulting 6- O -mesyl derivative gave benzyl 2-acetamido-3,4-di- O -benzyl-2-deoxy-6- O -mesyl-α- D -glucopyranoside which was treated with cesium fluoride in boiling 1,2-ethanediol to afford benzyl 2-acetamido-3,4-di- O -benzyl-2,6-dideoxy-6-fluoro-α- D -glucopyranoside ( 8 ). The benzyl groups of 8 were removed by hydrogenolysis to give 2-acetamido-2,6-dideoxy-6-fluoro-α- D -glucopyranose ( 10 ) with a total yield of ca . 15% based on the starting material 2-acetamido-2-deoxy- D -glucopyranose. The use of methyl protecting groups instead of benzyl ones appeared to be detrimental because the demethylation of methyl 2-acetamido-2,6-dideoxy-6-fluoro-3,4-di- O -methyl-α- D -glucopyranoside with boron trichloride gave only traces of 10 .