- Synthetic heparin pentasaccharides
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Preparation and use of synthetic monosaccharides, disaccharides, trisaccharides, tetrasaccharides and pentasaccharides useful for the preparation of synthetic heparinoids.
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- METHOD FOR PREPARING FULLY PROTECTION HEPARIN PENTASACCHARIDE AND INTERMEDIATE THEREOF
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Disclosed is a process for chemically synthesizing a pharmaceutical intermediate, in particular to a novel intermediate and novel process for synthesizing an anticoagulant drug fondaparinux sodium intermediate - full protection heparin pentasaccharide. The process has a high reaction efficiency and a simple reaction operation, and enables the reaction intermediate to be easily purified, thus being suitable for the industrialized production of the full protection heparin pentasaccharide.
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- Synthesis of 4′-deoxy-4′-fluoro neamine and 4′-deoxy-4′-fluoro 4′-epi neamine
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The syntheses of 4′-deoxy-4′-fluoro neamine and 4′-deoxy-4′-fluoro 4′-epi neamine from the readily available neamine and paromamine are described. Different approaches for the introduction of fluorine such as the use of DAST, sulfonic esters displacement,
- Hanessian, Stephen,Saavedra, Oscar M.,Vilchis-Reyes, Miguel A.,Llaguno-Rueda, Ana M.
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supporting information
p. 1166 - 1171
(2014/08/05)
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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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- AN EFFICIENT AND SCALABLE PROCESS FOR THE MANUFACTURE OF FONDAPARINUX SODIUM
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The present invention relates to a process for the synthesis of the Factor Xa anticoagulent Fondaparinux and related compounds. The invention relates, in addition, to efficient and scalable processes for the synthesis of various intermediates useful in the synthesis of Fondaparinux and related compounds.
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- Synthesis of the upstream terminal disaccharide of the O-antigenic polysaccharide of vibrio cholerae O37
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The terminal disaccharide of the O-antigenic polysaccharide of Vibrio cholerae O37, 4-O-methyl-α-D-QuiNAc-(1→4)-α-d-QuiNAc, was synthesized as methyl glycoside involving glycosylation between glycosyl donor ethyl 2-azido-3-O-benzyl-2,6-dideoxy-4-O-methyl-
- Mazumder, Koushik,Sarkar, Swarbhanu,Sen, Asish Kumar
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p. 673 - 685
(2013/05/22)
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- EFFICIENT AND SCALABLE PROCESS FOR THE MANUFACTURE OF FONDAPARINUX SODIUM
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The present invention relates to a process for the synthesis of the Factor Xa anticoagulent Fondaparinux and related compounds. The invention relates, in addition, to efficient and scalable processes for the synthesis of various intermediates useful in the synthesis of Fondaparinux and related compounds.
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- Synthesis of heparin oligosaccharides and their interaction with eosinophil-derived neurotoxin
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A convenient route for the synthesis of heparin oligosaccharides involving regioselective protection of d-glucosamine and a concise preparation of rare l-ido sugars from diacetone α-d-glucose is described. Stereoselective coupling of a d-glucosamine-derived trichloroacetimidate with a 1,6-anhydro-β-l-idopyranosyl 4-alcohol gave the desired α-linked disaccharide, which was used as repeating unit for dual chain elongation and termination. Stepwise assembly from the reducing to the non-reducing end with a d-glucosamine-derived monosaccharide as starting unit furnished the oligosaccharide skeletons having different chain lengths. A series of functional group transformations afforded the expected heparin oligosaccharides with 3, 5 and 7 sugar units. Interaction of these oligosaccharides with eosinophil-derived neurotoxin (EDN), a cationic ribonuclease and a mediator produced by human eosinophils, was further investigated. The results revealed that at 5 μg mL-1, the heptasaccharide has sufficiently strong interference to block EDN binding to Beas-2B cells. The tri- and pentasaccharides have moderate inhibitory properties at 50 μg mL-1 concentration, but no inhibition has been observed at 10 μg mL-1. The IC50 values of the tri-, penta- and heptasaccharides are 69.4, 47.2 and 0.225 μg mL-1, respectively.
- Hung, Shang-Cheng,Lu, Xin-An,Lee, Jinq-Chyi,Chang, Margaret Dah-Tsyr,Fang, Shun-Lung,Fan, Tan-Chi,Zulueta, Medel Manuel L.,Zhong, Yong-Qing
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experimental part
p. 760 - 772
(2012/02/05)
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- Synthesis of oligodiaminosaccharides having α-glycoside bonds and their interactions with oligonucleotide duplexes
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Syntheses of the novel oligodiaminosaccharides, α-(1→4)-linked- 2,6-diamino-2,6-dideoxy-d-glucopyranose oligomers, and their interactions with nucleic acid duplexes DNA-DNA, RNA-RNA, and DNA-RNA are described. Monomers to tetramers of oligodiaminoglucose
- Iwata, Rintaro,Sudo, Masafumi,Nagafuji, Kenta,Wada, Takeshi
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p. 5895 - 5906
(2011/10/09)
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- PROCESS FOR PREPARING FONDAPARINUX SODIUM AND INTERMEDIATES USEFUL IN THE SYNTHESIS THEREOF
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Processes for the synthesis of the Factor Xa anticoagulent Fondaparinux, and related compounds are described. Also described are protected pentasaccharide intermediates as well as efficient and scalable processes for the industrial scale production of Fondaparinux sodium by conversion of the protected pentasaccharide intermediates via a sequence of deprotection and sulfonation reactions.
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Page/Page column 34
(2011/05/08)
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- Oligo-Aminosaccharide compound
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An oligo-aminosaccharide compound formed by binding 3 to 6 saccharides, such as 2,6-diamino-2,6-dideoxy-α-(1→4)-D-glucopyranose oligomers, or a salt thereof, which has high affinity to a double-stranded nucleic acid.
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Page/Page column 8
(2011/01/12)
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- A 1-acetamido derivative of 6-epi-valienamine: An inhibitor of a diverse group of β-N-acetylglucosaminidases
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The synthesis of an analogue of 6-epi-valienamine bearing an acetamido group and its characterisation as an inhibitor of β-N- acetylglucosaminidases are described. The compound is a good inhibitor of both human O-GlcNAcase and human β-hexosaminidase, as well as two bacterial β-N-acetylglucosaminidases. A 3-D structure of the complex of Bacteroides thetaiotaomicron BtGH84 with the inhibitor shows the unsaturated ring is surprisingly distorted away from its favoured solution phase conformation and reveals potential for improved inhibitor potency. This journal is The Royal Society of Chemistry.
- Scaffidi, Adrian,Stubbs, Keith A.,Dennis, Rebecca J.,Taylor, Edward J.,Davies, Gideon J.,Vocadlo, David J.,Stick, Robert V.
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p. 3013 - 3019
(2008/04/01)
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- Toward synthesis of the regular sequence of heparin: synthesis of two tetrasaccharide precursors
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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.
- Zhou, Ying,Lin, Feng,Chen, Jianfang,Yu, Biao
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p. 1619 - 1629
(2007/10/03)
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- L-Iduronic acid derivatives as glycosyl donors
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O-[Methyl (2-O-acetyl-3-O-benzyl-4-O-levulinyl-α, and β-L-idopyranosid)uronate]trichloroacetimidate and the corresponding n-pentenyl glycosides are efficient L-iduronic acid glycosyl donors. Both have been used for the high-yielding synthesis of basic disaccharide blocks which are useful for the subsequent synthesis of complex oligosaccharides related to heparin/heparan sulfate, and dermatan sulfate. In contrast, the corresponding thioethyl glycosides, thiophenyl glycosides, and fluoride, did not yield the expected disaccharides.
- Tabeur, Christine,Machetto, Francoise,Mallet, Jean-Maurice,Duchaussoy, Philippe,Petitou, Maurice,Sinay, Pierre
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p. 253 - 276
(2007/10/03)
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