期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 53, 期 37, 页码 9876-9879出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201404154
关键词
anticoagulant; carbohydrates; heparin; one-pot reactions; total synthesis
资金
- Ministry of Science and Technology [NSC 100-2113-M-001-019-MY3, NSC 101-2628-M-001-006-MY3]
- National Health Research Institutes [NHRI-EX101-10146NI]
- Academia Sinica
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 -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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