Journal
CHEMMEDCHEM
Volume 9, Issue 5, Pages 1071-1080Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cmdc.201400019
Keywords
fondaparinux; glycosylation; heparin; pentasaccharides
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Funding
- National Basic Research Program of China (973 Program) [2010CB529106, 2012CB910300]
- Natural Science Foundation of China [21332006, 21372130]
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The anticoagulant pentasaccharide fondaparinux was synthesized using an improved and optimized synthetic strategy including a convergent [3+2] coupling approach, orthogonal protecting groups and various glycosyl donors. The new methods of glycosylation were also used for controlling the stereochemical configuration and improving the yield of the glycosylation. In addition, HPLC and NMR methods to monitor the process of total synthesis of fondaparinux were employed. This work provides a comprehensive elaboration for the synthesis and analysis of fondaparinux based on related literature, as well as abundant information for the synthesis of heparin-like oligosaccharides.
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