Accessing C-1 Phosphonylated 2-Acylamino Uronic Acids via 2-Nitro-glycals
Author(s)
Bhatt, Beenu
Thomson, Robin J
von Itzstein, Mark
Year published
2011
Metadata
Show full item recordAbstract
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 ߭L-gulo-configured phosphonate. Reversing the reaction order resulted in the exclusive formation of the ߭D-gluco-configured phosphonate. In both cases the thermodynamic 1,2-trans-di-equatorial phosphonylation product is obtained.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 ߭L-gulo-configured phosphonate. Reversing the reaction order resulted in the exclusive formation of the ߭D-gluco-configured phosphonate. In both cases the thermodynamic 1,2-trans-di-equatorial phosphonylation product is obtained.
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Journal Title
The Journal of Organic Chemistry
Volume
76
Issue
10
Copyright Statement
Self-archiving of the author-manuscript version is not yet supported by this journal. Please refer to the journal link for access to the definitive, published version or contact the author[s] for more information.
Subject
Medicinal and biomolecular chemistry
Organic chemistry
Organic chemical synthesis