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Total Synthesis of Anticoagulant Pentasaccharide Fondaparinux
Author(s) -
Li Tiehai,
Ye Hui,
Cao Xuefeng,
Wang Jiajia,
Liu Yonghui,
Zhou Lifei,
Liu Qiang,
Wang Wenjun,
Shen Jie,
Zhao Wei,
Wang Peng
Publication year - 2014
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.201400019
Subject(s) - fondaparinux , glycosylation , chemistry , yield (engineering) , glycosyl , combinatorial chemistry , stereochemistry , biochemistry , medicine , surgery , materials science , thrombosis , venous thromboembolism , metallurgy
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.