42926-91-0Relevant articles and documents
Method for synthesizing fondaparinux sodium monosaccharide intermediate
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, (2019/04/02)
The invention discloses a method for synthesizing a fondaparinux sodium monosaccharide intermediate. According to the method, a fondaparinux sodium monosaccharide fragment intermediate, namely 1,6-dehydro-3-O-benzyl-beta-L-idopyranose, is prepared by taki
METHODS AND INTERMEDIATES FOR THE PREPARATION OF FONDAPARINUX
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, (2014/01/08)
The present invention relates to methods for the synthesis of fondaparinux and intermediates thereto.
Synthesis of Fondaparinux: Modular synthesis investigation for heparin synthesis
Lin, Feng,Lian, Gaoyan,Zhou, Ying
, p. 32 - 39 (2013/05/09)
The anti-thromboembolic pentasaccharide Fondaparinux was synthesized in 36 steps for the longest linear route, with 0.017% overall yield from d-glucose. Only three kinds of protecting groups were used for hydroxyl protection, Bn, Ac, and Bz, to accomplish this complex synthesis without decreasing the synthetic efficiency. Three l-idopyranosyl donors were investigated. Thioethyl glycoside is an efficient donor for l-idopyranosyl glycosylation with full α-selectivity, while l-idopyranosyl trichloroacetimidate resulted in poor α/β selectivity. A practical synthesis of key intermediate 1,6-anhydro-l-idopyranose 17 by H+/β-CD catalyst was developed.
Synthesis of heparin oligosaccharides and their interaction with eosinophil-derived neurotoxin
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
, p. 760 - 772 (2012/02/05)
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.
An efficient synthesis of l-idose and l-iduronic acid thioglycosides and their use for the synthesis of heparin oligosaccharides
Tatai, Janos,Osztrovszky, Gyoergyi,Kajtar-Peredy, Maria,Fuegedi, Peter
, p. 596 - 606 (2008/09/21)
Efficient preparations of thioglycoside derivatives of l-idose and l-iduronic acid are described. The method avoids the tedious chromatographic separations of furanose and pyranose anomeric mixtures, and affords the thioglycosides in a stereoselective man
Synthesis of 48 disaccharide building blocks for the assembly of a heparin and heparan sulfate oligosaccharide library
Lu, Ng-Dai,Shie, Chi-Rung,Kulkarni, Suvarn S.,Pan, Guan-Rong,Lu, Xin-An,Hung, Shang-Cheng
, p. 5995 - 5998 (2007/10/03)
(Chemical Equation Presented) An efficient synthesis of the entire set of suitably protected 48 disaccharide building blocks for the assembly of a heparin and heparan sulfate oligosaccharide library is described here.
Synthesis of Heparin Oligosaccharides
Lee, Jinq-Chyi,Lu, Xin-An,Kulkarni, Suvarn S.,Wen, Yuh-Sheng,Hung, Shang-Cheng
, p. 476 - 477 (2007/10/03)
An efficient preparation of rare 2-O-benzoyl-3-O-benzyl-1,6-anhydro-β-l-idopyranose from commercially available diacetone α-d-glucose in five straightforward steps is described here. With this key building block in hand, the total syntheses of heparin oligosaccharides with three, five, seven, and nine sugar units are successfully carried out. Copyright
From D-Glucose to Biologically Potent L-Hexose Derivatives: Synthesis of α-L-Iduronidase Fluorogenic Detector and the Disaccharide Moieties of Bleomycin A2 and Heparan Sulfate
Lee, Jinq-Chyi,Chang, Shu-Wen,Liao, Chih-Cheng,Chi, Fa-Chen,Chen, Chien-Sheng,Wen, Yuh-Sheng,Wang, Cheng-Chung,Kulkarni, Suvarn S.,Puranik, Ramachandra,Liu, Yi-Hung,Hung, Shang-Cheng
, p. 399 - 415 (2007/10/03)
A novel and convenient route for the synthesis of biologically potent and rare L-hexose derivatives from D-glucose is described. Conversion of diacetone-α-D-glucose (14) into 1,2:3,5-di-O-isopropylidene-β -L-idofuranose (19) was efficiently carried out in two steps. Orthogonal isopropylidene rearrangement of compound 19 led to 1,2:5,6-di-O-isopropylidene-β-L-idofuranose (27), which underwent regioselective epimerization at the C3 position to give the L-talo- and 3-functionalized L-idofuranosyl derivatives. Hydrolysis of compound 19 under acidic conditions furnished 1,6-anhydro-β-L-idopyranose (35) in excellent yield, which was successfully transformed into the corresponding L-allo, L-altro, L-gulo, and L-ido derivatives via regioselective benzylation, benzoylation, triflation and nucleophilic substitution as the key steps. Applications of these 1,6-anhydro-β-L-hexopyranoses as valuable building blocks to the syntheses of 4-methylcoumarin-7-yl-α-L-iduronic acid and the disaccharide moieties of bleomycin A2 as well as heparan sulfate are highlighted.
Biologically potent L-hexoses and 6-deoxy-L-hexoses: Their syntheses and applications
Kulkarni, Suvarn S.,Chi, Fa-Chen,Hung, Shang-Cheng
, p. 1193 - 1200 (2007/10/03)
This account describes our recent work in the development of new methodologies to prepare rare and biologically potent L-hexoses and 6-deoxy-L-hexoses, from cheapest D-glucose, via L-hexofuranoses and 1,6-anhydro-β-L-hexopyranoses as key building blocks. Their applications in the syntheses of heparin oligosaccharides, the carbohydrate moiety of bleomycin A2, and L-acovenose are also summarized here.