- Preparation method of fondaparinux sodium disaccharide intermediate
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The invention discloses a preparation method of fondaparinux sodium disaccharide intermediate. 1-O-substituent sulfonyl-2,3-bis-O-benzyl-4,6-O-benzylidene-beta-D-glucopyranose directly reacts with 1,6-dehydrated-2-deoxy-2-azido-3-O-acetyl-beta-D-glucopyranose to prepare the fondaparinux sodium disaccharide intermediate as shown in a formula I; and meanwhile, the fondaparinux sodium intermediate asshown in the formula I can be used as a raw material to synthesize fondaparinux sodium intermediate as shown in a formula IV. The preparation method is simple and small in steps, the yield is high, the atomic utilization rate is high, the three wastes are small, and the preparation method is suitable for industrial large-scale production. Please see the description for the formula.
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- Novel technology for preparing disaccharide fragment of fondaparinux sodium intermediate
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The invention relates to a novel technology for preparing disaccharide fragment of an anticoagulant drug fondaparinux sodium intermediate. The technology has the advantages of short reaction route, high efficiency, and easy purifying of the intermediate, and is suitable for commercial production of the full protection heparin pentasaccharide.
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- Total synthesis of anticoagulant pentasaccharide fondaparinux
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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.
- Li, Tiehai,Ye, Hui,Cao, Xuefeng,Wang, Jiajia,Liu, Yonghui,Zhou, Lifei,Liu, Qiang,Wang, Wenjun,Shen, Jie,Zhao, Wei,Wang, Peng
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p. 1071 - 1080
(2014/05/20)
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- PROCESS FOR THE PREPARATION OF DISACCHARIDES APPLIED TO HEPARIN PENTASACCHARIDES
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The invention provides an intermediate of formula (I) and the process for making the same. This intermediate is useful in the process for making polysaccharides, and more particularly fondaparinux.
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Page/Page column 7
(2012/04/23)
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- A facile preparation of uronates via selective oxidation with TEMPO/KBr/Ca(OCl)2 under aqueous conditions
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Addition of solid Ca(OCl)2 as the terminal oxidant in the TEMPO-mediated selective oxidation has the benefit of easier operation. A variety of partially protected saccharide derivatives (1a-l) have been successfully converted into the corresponding uronate derivatives, including disaccharide building blocks for GAG fragments and precursors to saponins. The beneficial effect of Aliquat 336 was also disclosed in the oxidation of certain substrates.
- Lin, Feng,Peng, Wenjie,Xu, Wen,Han, Xiuwen,Yu, Biao
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p. 1219 - 1223
(2007/10/03)
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- Synthesis, from cellobiose, of a trisaccharide closely related to the GlcNAc----GlcA----GlcN segment of the antithrombin-binding sequence of heparin.
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O-(2-Deoxy-2-sulfamido-6-O-sulfo-alpha-D-glucopyranosyl)-(1----4)- O-(beta-D- glucopyranosyluronic acid)-(1----4)-1,6-anhydro-2-deoxy-2-sulfamido-6-O-sulfo-beta-D-gl ucopyranose pentasodium salt (14) was synthesized as a heparin-related oligosaccharide. The glycosyl acceptor (derived from cellobiose) and a glycosyl donor, 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-alpha-D-glucopyranosyl bromide, were coupled in the presence of mercuric bromide and molecular sieves 4A to afford a 69% yield of fully protected trisaccharide, namely, O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-alpha-D-glucopyranosyl)-(1 ----4)- O-(methyl 2,3-di-O-benzyl-beta-D-glucopyranosyluronate)-(1----4)-3-O-acetyl- 1,6-anhydro-2 - azido-2-deoxy-beta-D-glucopyranose (10), which was converted into the partially sulfated trisaccharide 14. Compound 10 also underwent acetolysis to afford the glycosyl acetate, for further elongation of the glycosyl chain.
- Ichikawa,Ichikawa,Kuzuhara
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p. 273 - 282
(2007/10/02)
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