Synthesis of the Heparin‐Based Anticoagulant Drug Fondaparinux |
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Authors: | Dr Cheng‐Hsiu Chang Larry S Lico Dr Teng‐Yi Huang Dr Shu‐Yi Lin Dr Chi‐Liang Chang Prof?Dr Susan D Arco Prof?Dr Shang‐Cheng Hung |
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Institution: | 1. Genomics Research Center, Academia Sinica, No. 128 Academia Road, Section 2, Taipei 115 (Taiwan);2. Department of Chemistry, National Tsing Hua University, No. 101, Section 2, Kuang‐Fu Road, Hsinchu 300 (Taiwan);3. Institute of Chemistry, University of the Philippines, Diliman, Quezon City 1101 (Philippines) |
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Abstract: | Fondaparinux, a synthetic pentasaccharide based on the heparin antithrombin‐binding domain, is an approved clinical anticoagulant. Although it is a better and safer alternative to pharmaceutical heparins in many cases, its high cost, which results from the difficult and tedious synthesis, is a deterrent for its widespread use. The chemical synthesis of fondaparinux was achieved in an efficient and concise manner from commercially available D ‐glucosamine, diacetone α‐D ‐glucose, and penta‐O‐acetyl‐D ‐glucose. The method involves suitably functionalized building blocks that are readily accessible and employs shared intermediates and a series of one‐pot reactions that considerably reduce the synthetic effort and improve the yield. |
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Keywords: | anticoagulant carbohydrates heparin one‐pot reactions total synthesis |
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