87326-74-7

Basic information

• Product Name: (S)-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-trifluoromethanesulfonyloxy-acetic acid methyl ester
• Synonyms: (S)-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-trifluoromethanesulfonyloxy-acetic acid methyl ester
• CAS NO: 87326-74-7
• Molecular Weight: 470.421
• Mol File: 87326-74-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S)-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-trifluoromethanesulfonyloxy-acetic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-trifluoromethanesulfonyloxy-acetic acid methyl ester(87326-74-7)
• EPA Substance Registry System: (S)-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-trifluoromethanesulfonyloxy-acetic acid methyl ester(87326-74-7)

Safety Data

• Hazardous Substances Data: 87326-74-7(Hazardous Substances Data)

Upstream product

• 92955-34-5 5-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-6-O-trityl-α-D-glucofuranose 
• 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 
• 106445-04-9 1-(6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(tert-butyldimethylsiloxy)ethanol 
• 87326-72-5 3-O-benzyl-1,2-O-isopropyridene-α-D-glucofuranuronic acid 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 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 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 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 

Downstream Products

• 87326-75-8 (R)-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-trifluoromethanesulfonyloxy-acetic acid methyl ester 
• 444118-40-5 methyl 3-O-benzyl-1,2-O-isopropylidene-5-O-levulinoyl-β-L-idofuranosyluronate 
• 444118-87-0 methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-β-L-idopyranosyluronate trichloroacetimidate 
• 87326-77-0 methyl 3-O-benzyl-L-idopyranosyluronate 
• 444118-44-9 1,2-O-isopropylidene-3-O-benzyl-4-O-trichloroacetyl-6-methyl-α-L-idonic acid 
• 444118-45-0 methyl 3-O-benzyl-1,2-O-cyclopentylidene-β-L-idopyranosyluronate 
• 444118-54-1 3,6-di-O-acetyl-2-azido-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-isopropylidene-β-L-idopyranosyluronate 
• 444118-53-0 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-isopropylidene-β-L-idopyranosyluronate 
• 444118-55-2 3,6-di-O-acetyl-2-azido-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-cyclopentylidene-β-L-idopyranosyluronate 
• 444119-08-8 methyl 3-O-benzyl-4-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-β-L-idopyranosyluronate 
• 444119-10-2 methyl 1,2-di-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α/β-L-idopyranosyluronate 
• 444118-71-2 3,6-di-O-acetyl-2-azido-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 1,2-di-O-acetyl-3-O-benzyl-α/β-L-idopyranosyluronate 
• 525593-53-7 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-isopropylidene-β-L-idopyranosyluronate 

Relevant articles and documents

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.

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.