87326-72-5

Upstream product

• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 106445-04-9 1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethanol 
• 100-44-7 benzyl chloride 
• 37073-70-4 1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-trityloxyethanol 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 177897-33-5 Acetic acid (R)-1-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-ethyl ester 
• 100-39-0 benzyl bromide 
• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 
• 92955-34-5 5-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-6-O-trityl-α-D-glucofuranose 

Downstream Products

• 87326-73-6 (S)-methyl 2-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-hydroxyacetate 
• 87907-09-3 methyl 3-O-benzyl-4-O-monochloroacetyl-β-L-idopyranuronate 1,2-(tert-butyl orthoacetate) 
• 87326-83-8 methyl 3-O-benzyl-β-L-idopyranuronate 1,2-(tert-butyl orthoacetate) 
• 87326-82-7 methyl 4-O-acetyl-3-O-benzyl-β-L-idopyranuronate 1,2-(tert-butyl orthoacetate) 
• 87907-08-2 C₁₈H₂₁BrO₈ 
• 93382-47-9 methyl (acetyl 2,4-di-O-acetyl-3-O-benzyl-α,β-L-idopyranoside)uronate 
• 444118-88-1 pent-4-enyl (methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosyluronate)-(1->4)-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate 
• 444118-91-6 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyl-(1->4)-(3,6-di-O-acetyl-2-azido-2-deoxy-α/β-D-glucopyranosyl trichloroacetimidate 
• 444118-90-5 tert-butyldimethylsilyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-(methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyl)-(1->4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranoside 
• 525593-61-7 pent-4-enyl (6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-β-D-glucopyranosyl)-(1->4)-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyl)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 444118-89-2 pent-4-enyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate 
• 444118-67-6 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 2-O-levulinoyl-3-O-benzyl-α-D-glucopyranosyluronate trichloroacetimidate 
• 444118-62-1 tert-butyldimethylsilyl (6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate 
• 444118-69-8 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-α-D-glucopyranosyluronate trichloroacetimidate 

Relevant academic research and scientific papers

A chemoselective oxidation of monosubstituted ethylene glycol: Facile synthesis of optically active α-hydroxy acids

A mild and efficient method for the synthesis of optically active α-hydroxy acids through chemoselective oxidation of monosubstituted ethylene glycols using the TEMPO-NaOCl reagent system is described. It is evident from our studies that the solvent, pH and reaction temperature are very crucial for the success of this oxidation. The versatility of this method has been demonstrated with a variety of aliphatic, aromatic and carbohydrate substrates bearing various functional groups. the Partner Organisations 2014.

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.

PROCESS FOR PREPARATION OF FONDAPARINUX AND ITS INTERMEDIATES

The present invention relates to a process for the preparation of 3-O-benzyl- 1,2-O- isopropylidene-α-D-glucofuranuronic acid (Formula IV) and ester (Formula V) thereof. The process comprises benzylation of l,2:5,6-di-O-isopropylidene-α-D-glucofuranose (Formula I; hereinafter, referred to as diacetone-D-glucose) in the presence of tetrabutylammonium bromide, followed by selective hydrolysis of the product formed (Formula II) using sulfuric acid to obtain 3-O-benzyl- 1,2-O-isopropylidene-α-D- glucofuranose (Formula III). Compound of Formula III is then oxidized to compound of Formula IV which upon esterification provides corresponding ester of Formula V. The process of the invention can be used in the production of fondaparinux sodium, a heparin and blood clotting factor Xa inhibitor.(Formula I, II, III, IV, V) (I) (II) (III) (IV) (V) wherein R is optionally branched alkyl group.

Modular synthesis of heparin oligosaccharides

A general, modular strategy for the first completely stereoselective synthesis of defined heparin oligosaccharides is described. Six monosaccharide building blocks (four differentially protected glucosamines, one glucuronic and one iduronic acid) were uti

SYNTHESIS OF HEPARIN FRAGMENTS. A CHEMICAL SYNTHESIS OF THE TRISACCHARIDE O-(2-DEOXY-2-SULFAMIDO-3,6-DI-O-SULFO-α-D-GLUCOPYRANOSYL)-(1->4)-O-(2-O-SULFO-α-L-IDOPYRANOSYL-URONIC ACID)-(1->4)-2-DEOXY-2-SULFAMIDO-6-O-SULFO-D-GLUCOPYRANOSE HEPTASODIUM SALT

Known 3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose was first converted into methyl 3-O-benzyl-1,2-O-isopropylidene-β-L-idofuranuronate.Acid hydrolysis, followed by acetylation and treatment with titanium tetrabromide, gave methyl (2,4-di-O-acetyl-3-O-benzyl-α-L-idopyranosyl bromide)uronate, which was immediately transformed into methyl 4-O-acetyl-3-O-benzyl-β-L-idopyranuronate 1,2-(tert-butyl orthoacetate).A two-step replacement of the 4-O-acetyl by a 4-O-chloroacetyl group gave the key derivative, crystalline methyl 3-O-benzyl-4-O-chloroacetyl-β-L-idopyranuronate 1,2-(tert-butyl orthoacetate).Condensation of this orthoester with an excess of crystalline benzyl 6-O-acetyl-3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside in chlorobenzene in the presence of 2,6-dimethylpyridinium perchlorate gave crystalline benzyl 6-O-acetyl-3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-α-D-glucopyranoside in 40 percent yield.O-Demonochloroacetylation, followed by condensation with known 3,6-di-O-acetyl-2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl bromide in dichloromethane in the presence of 2,4,6-trimethylpyridine, silver triflate, and molecular sieve provided benzyl O-(3,6-di-O-acetyl-2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-6-O-acetyl-3-O-benzyl-2-(benzyloxycarbonyl)amino-2-deoxy-α-D-glucopyranoside in 88 percent yield.O-Deacetylation with sodium hydroxide, followed successively by O-sulfation in N,N-dimethylformamide in the presence of sulfur trioxide-trimethylamine complex, catalytic hydrogenolysis, and N-sulfation in water with the same sulfating agent, gave the heptasodium salt of O-(2-deoxy-2-sulfamido-3,6-di-O-sulfo-α-D-glucopyranosyl)-(1->4)-O-(2-O-sulfo-α-L-idopyranosyluronic acid)-(1->4)-2-deoxy-2-sulfamido-6-O-sulfo-D-glucopyranose.This trisaccharide, which is a fragment of the minimal antithrombin III-binding region in heparin, neither binds to antithrombin III nor induces anti-Xa activity.