Brecanavir

Base Information

• Chemical Name: Brecanavir
• CAS No.: 313682-08-5
• Deprecated CAS: 675184-03-9
• Molecular Formula: C33H41 N3 O10 S2
• Molecular Weight: 703.835
• UNII: E367I8C7FI
• DSSTox Substance ID: DTXSID10185296
• Nikkaji Number: J2.116.964A
• Wikipedia: Brecanavir
• Wikidata: Q4959983
• NCI Thesaurus Code: C76908
• Metabolomics Workbench ID: 144532
• ChEMBL ID: CHEMBL206031
• Mol file: 313682-08-5.mol

Synonyms:(1S,2R)-3-((1,3-benzodioxol-5-ylsulfonyl)(2-methylpropyl)amino-2-hydroxy-1-((4-(2-methyl-4-thiazolyl)methoxy)phenyl)methylpropyl)carbamic acid, hexahydrofuro(2,3-b)furan-3yl ester;brecanavir;VX-385;VX385

Chemical Property of Brecanavir

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 191.60000
• Density: 1.43g/cm³
• LogP: 5.33740
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 15
• Exact Mass: 703.22333686
• Heavy Atom Count: 48
• Complexity: 1150

Purity/Quality:

≥98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC(=CS1)COC2=CC=C(C=C2)CC(C(CN(CC(C)C)S(=O)(=O)C3=CC4=C(C=C3)OCO4)O)NC(=O)OC5COC6C5CCO6
• Isomeric SMILES: CC1=NC(=CS1)COC2=CC=C(C=C2)C[C@@H]([C@@H](CN(CC(C)C)S(=O)(=O)C3=CC4=C(C=C3)OCO4)O)NC(=O)O[C@H]5CO[C@@H]6[C@H]5CCO6
• Recent ClinicalTrials: A Dose Ranging Study Of GW640385 Boosted With Ritonavir (Rtv) In Comparison To A RTV-Boosted Protease Inhibitor (PI) In HIV-1 Infected PI-Experienced Adults
• Recent EU Clinical Trials: A Phase IIB, Randomized, Multicenter, Parallel Group Study to Evaluate the Short-Term Safety, Pharmacokinetics and Antiviral Activity of Four Blinded Dosing Regimens of GW640385/Ritonavir Therapy Compared to Open-label Current Protease Inhibitor (PI) therapy in HIV-1 Infected, PI Experienced Adults for 2 weeks with Long-Term Evaluation (> 48 weeks) of Safety, Pharmacokinetic and Antiviral Activity of Selected GW640385/RTV Dosing Regimen(s) vs. a Ritonavir-boosted, PI Containing Regimen
• Uses: Treatment of HIV infection in combination with other antiretroviral agents.

Technology Process of Brecanavir

There total 5 articles about Brecanavir which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 36.0%

→ brecanavir (313682-08-5)

Guidance literature:

Reference yield:

(3R,3AS,6AR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-1-[4-(benzyloxy)benzyl]-2-hydroxypropylcarbamate (313679-55-9) → brecanavir (313682-08-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 60 percent / PTSA / CH₂Cl₂

2: 95 percent / H₂ / Pd/C / tetrahydrofuran

3: Cs₂CO₃ / dimethylformamide

4: aq. HCl / dioxane

With hydrogenchloride; hydrogen; caesium carbonate; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2006.01.035

Reference yield:

N-(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl-oxycarbonyl-, (4S,5R)-4-(4-benzyloxy-benzyl)-5-i-butyl-[(3,4-methylenedioxyphenyl)sulfonyl]-aminomethyl-2,2-dimethyl-oxazolidine (313682-03-0) → brecanavir (313682-08-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / H₂ / Pd/C / tetrahydrofuran

2: Cs₂CO₃ / dimethylformamide

3: aq. HCl / dioxane

With hydrogenchloride; hydrogen; caesium carbonate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2006.01.035

upstream raw materials:

N-(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl-oxycarbonyl-(4S,5R)-4-[4-(2-methylthiazolo-4-methyloxy)-benzyl]-5-i-butyl-[(3,4-methylenedioxyphenyl)sulfonyl]-aminomethyl-2,2-dimethyl-oxazolidine

(3R,3AS,6AR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-1-[4-(benzyloxy)benzyl]-2-hydroxypropylcarbamate

(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl (4S,5R)-5-{[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]methyl}-4-(4-hydroxybenzyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

N-(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl-oxycarbonyl-, (4S,5R)-4-(4-benzyloxy-benzyl)-5-i-butyl-[(3,4-methylenedioxyphenyl)sulfonyl]-aminomethyl-2,2-dimethyl-oxazolidine

Downstream raw materials:

(10R)-10-((1S)-1-({[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl}amino)-2-{4-[(2-methyl-1,3-thiazol-4-yl)methoxy]phenyl}ethyl)-12-(1,3-benzodioxol-5-ylsulfonyl)-14-methyl-8-oxo-3,6,9-trioxa-12-azapentadecan-1-oic acid

{2-[((1R,2S)-2-({[(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yloxy]carbonyl}amino)-1-{[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]methyl}-3-{4-[(2-methyl-1,3-thiazol-4-yl)methoxy]phenyl}propyl)oxy]-2-oxoethoxy}acetic acid

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