title: Total synthesis of anticoagulant pentasaccharide fondaparinux.
abstract: 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.
authors.affiliation: State Key Laboratory of Medicinal Chemical Biology and College of Pharmacy, Nankai University, Synergetic Innovation Center of Chemical Science and Engineering (Tianjin), 94 Weijin Road, Tianjin 300071 (P.R. China).
authors.forename: Tiehai
authors.initials: T
authors.lastname: Li
authors.forename: Hui
authors.initials: H
authors.lastname: Ye
authors.forename: Xuefeng
authors.initials: X
authors.lastname: Cao
authors.forename: Jiajia
authors.initials: J
authors.lastname: Wang
authors.forename: Yonghui
authors.initials: Y
authors.lastname: Liu
authors.forename: Lifei
authors.initials: L
authors.lastname: Zhou
authors.forename: Qiang
authors.initials: Q
authors.lastname: Liu
authors.forename: Wenjun
authors.initials: W
authors.lastname: Wang
authors.forename: Jie
authors.initials: J
authors.lastname: Shen
authors.forename: Wei
authors.initials: W
authors.lastname: Zhao
authors.forename: Peng
authors.initials: P
authors.lastname: Wang
mesh_terms: D000925:Anticoagulants / Q000138:chemical synthesis* / Q000737:chemistry; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D003500:Cyclization; D000077425:Fondaparinux; D006031:Glycosylation; D008969:Molecular Sequence Data; D011134:Polysaccharides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000925:Anticoagulants; D011134:Polysaccharides; D000077425:Fondaparinux
keywords: fondaparinux; glycosylation; heparin; pentasaccharides