616876-73-4Relevant academic research and scientific papers
Total synthesis of anticoagulant pentasaccharide fondaparinux
Li, Tiehai,Ye, Hui,Cao, Xuefeng,Wang, Jiajia,Liu, Yonghui,Zhou, Lifei,Liu, Qiang,Wang, Wenjun,Shen, Jie,Zhao, Wei,Wang, Peng
, p. 1071 - 1080 (2014/05/20)
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. A matter of protection! The anticoagulant pentasaccharide fondaparinux was synthesized using an improved and optimized synthetic strategy. The process of total synthesis was monitored by HPLC and NMR. This work will contribute to continued improvement of the multistep production of fondaparinux and provide abundant information for the synthesis of heparin-like oligosaccharides.
Synthesis and scalable conversion of L-iduronamides to heparin-related Di- and tetrasaccharides
Hansen, Steen U.,Miller, Gavin J.,Barath, Marek,Broberg, Karl R.,Avizienyte, Egle,Helliwell, Madeleine,Raftery, James,Jayson, Gordon C.,Gardiner, John M.
, p. 7823 - 7843 (2013/01/15)
A diastereomerically pure cyanohydrin, preparable on kilogram scale, is efficiently converted in one step into a novel L-iduronamide. A new regioselective acylation of this iduronamide and a new mild amide hydrolysis method mediated by amyl nitrite enable
Toward synthesis of the regular sequence of heparin: synthesis of two tetrasaccharide precursors
Zhou, Ying,Lin, Feng,Chen, Jianfang,Yu, Biao
, p. 1619 - 1629 (2007/10/03)
Two fully protected tetrasaccharides, which represent precursors for the synthesis of the regular sequence of heparin, were synthesized via coupling of a pair of disaccharide trichloroacetimidates with a thioglycoside and a glucosamine derivative, respectively, in a sequential manner.
A modular strategy toward the synthesis of heparin-like oligosaccharides using monomeric building blocks in a sequential glycosylation strategy
Codee, Jeroen D. C.,Stubba, Bas,Schiattarella, Marialuisa,Overkleeft, Herman S.,Van Boeckel, Constant A. A.,Van Boom, Jacques H.,Van Der Marel, Gijsbert A.
, p. 3767 - 3773 (2007/10/03)
A novel flexible assembly strategy is described for the modular synthesis of heparin and heparan sulfates. The reported strategy uses monomeric building bocks to construct the oligosaccharide chain to attain a maximum degree of flexibility. In the assembly, 1-hydroxyl glucosazido- and 1-thio uronic acid donors are combined in a sequential glycosylation protocol using sulfonium triflate activator systems. The key 1-thio uronic acids were obtained in an efficient manner from diacetone glucose employing a chemo- and regioselective oxidation of partially protected glucose and idose thioglycosides.
Some key experimental features of a modular synthesis of heparin-like oligosaccharides
De Paz, Jose-Luis,Ojeda, Rafael,Reichardt, Niels,Martin-Lomas, Manuel
, p. 3308 - 3324 (2007/10/03)
The key features of a modular n+2 strategy for a completely stereoselective synthesis of oligosaccharides containing the GlcN-IdoA repeating unit of the major sequence of heparin are presented and discussed in detail. These key features include the regio-
