摘要

Peracetylated 3-deoxy-3-fluoro analogues of d-glucosamine and d-galactosamine 3 and 4, respectively, were prepared from 1,6:2,3-dianhydro-4-O-benzyl--d-mannopyranose (6). Azidolysis of 6 followed by reaction with diethylaminosulfur trifluoride gave 1,6-anhydro-2-azido-4-O-benzyl-2,3-dideoxy-3-fluoro--d-glucopyranose (9). Cleavage of the internal acetal, hydrogenation and acetylation yielded 3. De-O-benzylation of 9 followed by a configurational inversion at C4 gave 1,6-anhydro-2-azido-2,3-dideoxy-3-fluoro--d-galactopyranose (18), which provided 4 after cleavage of the 1,6-anhydro bridge, reduction, and acetylation.

  • 出版日期2014-6