Accessing C-1 phosphonylated 2-acylamino uronic acids via 2-nitro-glycals |
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Authors: | Bhatt Beenu Thomson Robin J von Itzstein Mark |
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Institution: | Institute for Glycomics, Griffith University, Gold Coast Campus, Queensland 4222, Australia. |
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Abstract: | 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 β-L-gulo-configured phosphonate. Reversing the reaction order resulted in the exclusive formation of the β-D-gluco-configured phosphonate. In both cases the thermodynamic 1,2-trans-di-equatorial phosphonylation product is obtained. |
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