87326-68-9

Upstream product

• 850637-35-3 3-O-acetyl-1,6-anhydro-2-azido-4-O-tert-butyldiphenylsilyl-2-deoxy-β-D-glucopyranose 
• 88261-50-1 1,6:2,3-dianhydro-4-O-tert-butyldimethylsilyl-β-D-mannopyranose 
• 3868-03-9 1,6:2,3-dianhydro-β-D-mannopyranose 
• 88261-51-2 1,6-anhydro-2-azide-4-O-(tert-buthyldimethylsilyl)-2-deoxy-β-D-glucopyranose 
• 67546-20-7 1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 
• 186967-38-4 3-O-acetyl-1,6-anhydro-2-azido-4-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose 
• 139437-39-1 1,6-anhydro-2-deoxy-2-iodo-β-D-glucopyranose 
• 2873-29-2 D-glucal triacetate 
• 492-62-6 alpha-D-glucopyranose 
• 604-68-2 α-D-glucopyranose peracetylate 
• 67313-50-2 1,6:2,3-dianhydro-4-O-(tetrahydropyran-2-yl)-β-D-mannopyranose 

Downstream Products

• 104530-54-3 (2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-3-(2-chloro-acetoxy)-6-((2R,3S,4R,5R)-4,6-diacetoxy-2-acetoxymethyl-5-azido-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 87907-05-9 (2S,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-4-Acetoxy-2-acetoxymethyl-5-azido-6-bromo-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 87907-02-6 O-(methyl 2,3-di-O-benzyl-4-O-(chloroacetyl)-β-D-glucopyranosyluronate)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 
• 135362-96-8 O-(6-O-acetyl-2-azide-3,4-di-O-benzyl-2-deoxy-2-α-D-glucopyranosyl)-(1→4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranosyl trichloroacetimidate 
• 135362-95-7 O-(6-O-acetyl-2-azide-3,4-di-O-benzyl-2-deoxy-2-α-D-glucopyranosyl)-(1→4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl trichloroacetimidate 
• 99541-27-2 O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 
• 99541-26-1 O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose 
• 1262887-52-4 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-benzyl (3-O-benzyl-2-O-levulinoyl)-β-D-glucopyranosyluronate-(1->4)-(3-O-acetyl-1,6-anhydro-2-azido)-2-deoxy-β-D-glucopyranose 

Relevant academic research and scientific papers

A method for synthesizing intermediate the sulphur reaches the liver last of the ten Heavenly Stems sodium

The invention discloses a synthetic method of a fondaparinux sodium intermediate. The synthetic method comprises the following steps: by using a compound 3 as a raw material, performing hydroxyl acetylation to obtain a compound 6, and removing p-methoxybenzyl (PMB) of the compound 6 by using ammonium cerium nitrate to obtain a Monomer C ring. By virtue of the mode, compared with a conventional five-step method for synthesizing the Monomer C ring, the synthetic method of the fondaparinux sodium intermediate, disclosed by the invention, can be used for simplifying the synthetic route of the Monomer C ring and reducing the production cost, and is suitable for large-scale industrial production.

Total synthesis of anticoagulant pentasaccharide fondaparinux

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.

PROCESS FOR PREPARING HEPARINOIDS AND INTERMEDIATES USEFUL IN THE SYNTHESIS THEREOF

Processes are disclosed for the synthesis of the Factor Xa anticoagulant fondaparinux and related compounds. Protected pentasaccharide intermediates and 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 are provided.

NOVEL ANTI-INFLAMMATORY PRO-DRUGS

The present invention relates to compounds according to formula (I): wherein R is selected from the group consisting of anti-inflammatory agents and pharmaceutically acceptable salts thereof, pharmaceutical compositions comprising compounds of formula (I) and the use of these pharmaceutical compositions for the treatment or prophylaxis of chronic inflammatory diseases, in particular those that are caused by chronically activated macrophages. The chronic inflammatory disease is in particular atherosclerosis, (rheumatoid) arthritis, an (auto)immune disease or sarcoidosis.

Synthesis of 5-thio-L-fucose-containing disaccharides, as sequence-specific inhibitors, and 2'-fucosyllactose, as a substrate of α-L-fucosidases

Four 5-thio-L-fucose-containing disaccharides having α(1→6), α(1→3), α(1→4)GlcNAc, and α(1→2)Gal linkages (compounds 1-4, respectively) were synthesized as potential α-L-fucosidase inhibitors. The glycosylation reactions using 2,3,4-tri-O-acetyl-5-thio-L-fucopyranosyl trichloroacetimidate as a glycosyl donor and BF3·OEt2 as a catalyst gave mainly α-linked disaccharides. Only α(1→2)-linked disaccharide 4 showed inhibitory activity (K(i) = 0.21 mM) against Bacillus α-L-fucosidase which hydrolyzes the Fucα(1→2) linkage specifically. The results suggested that sequence specificity of an enzyme could be estimated from the inhibitory activities of the compounds 1-4. In contrast, every disaccharide showed inhibitory activity (K(i) = 30-91 μM) against bovine epididymis α-L-fucosidase.

t-BUTYLDIMETHYLSILYL (TBDMS) AS PROTECTIVE GROUP IN CARBOHYDRATE CHEMISTRY MIGRATION OF THE TBDMS GROUP IN TRANS-DIOL SYSTEMS

In the presence of base the t-butyldimethylsilyl (TBDMS) protective group is able to migrate between trans-diaxial hydroxyl functions of carbohydrates.