Accessing C-1 Phosphonylated 2-Acylamino Uronic Acids via 2-Nitro-glycals

作者:Bhatt Beenu; Thomson Robin J; von Itzstein Mark*
来源:Journal of Organic Chemistry, 2011, 76(10): 4099-4104.
DOI:10.1021/jo2002193

摘要

Two approaches are described for the synthesis of 2-acylamino uronic acid glycosyl phosphonates from readily accessible D-glucal. The first approach that entailed oxidation of the C-6 hydroxyl group followed by phosphonylation of the uronate 2-nitro-glycal, resulted in the formation of the beta-L-gulo-configured phosphonate. Reversing the reaction order resulted in the exclusive formation of the beta-D-gluco-configured phosphonate. In both cases the thermodynamic 1,2-trans-di-equatorial phosphonylation product is obtained.

  • 出版日期2011-5-20