Deoxoartemisinin

Base Information

• Chemical Name: Deoxoartemisinin
• CAS No.: 126189-95-5
• Molecular Formula: C15H24 O4
• Molecular Weight: 268.353
• Nikkaji Number: J304.249I
• ChEMBL ID: CHEMBL273441
• Mol file: 126189-95-5.mol

Synonyms:10-deoxoartemisinin;artemisinin, 10-deoxo;deoxoartemisinin;deoxodeoxyartemisinin;deoxoqinghaosu

Chemical Property of Deoxoartemisinin

Chemical Property:

• Vapor Pressure: 0.000305mmHg at 25°C
• Boiling Point: 373°Cat760mmHg
• Flash Point: 179.4°C
• PSA: 47.92000
• Density: 1.15g/cm³
• LogP: 2.42440
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 268.16745924
• Heavy Atom Count: 19
• Complexity: 386

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2C(COC3C24C1CCC(O3)(OO4)C)C
• Isomeric SMILES: C[C@@H]1CC[C@H]2[C@H](CO[C@H]3[C@@]24[C@H]1CC[C@](O3)(OO4)C)C

Technology Process of Deoxoartemisinin

There total 48 articles about Deoxoartemisinin 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: 71.0%

artemisinin (63968-64-9,113472-97-2,119241-68-8) → (+)-deoxyartemisinin (126189-95-5)

Guidance literature:

With sodium tetrahydroborate; boron trifluoride diethyl etherate; In tetrahydrofuran; for 0.166667h; Heating;

DOI:10.1021/jm00167a036

Reference yield: 69.0%

2-(5,9-dimethyl-10,11,13-trioxatricyclo[7.2.2.01,6]tridec-2-yl)propan-1-ol (613233-67-3) → (+)-deoxyartemisinin (126189-95-5)

Guidance literature:

With [bis(acetoxy)iodo]benzene; iodine; In cyclohexane; at 20 ℃; Reagent/catalyst; Temperature;

DOI:10.1002/chem.201300076

Reference yield: 32.0%

2-(5,9-dimethyl-10,11,13-trioxatricyclo[7.2.2.01,6]tridec-2-yl)propan-1-ol (613233-67-3) + bis-[(trifluoroacetoxy)iodo]benzene (2712-78-9) → C17H25F3O5 + (+)-deoxyartemisinin (126189-95-5)

Guidance literature:

With iodine; In cyclohexane; at 20 ℃; for 35h;

DOI:10.1002/chem.201300076

upstream raw materials:

4-((4R,4aS,7R)-4,7-Dimethyl-4,4a,5,6,7,8-hexahydro-3H-isochromen-8-yl)-butan-2-one

artemisinin

C₁₂H₁₃O₂(CH₃)3(O)(OO)

4-((4R,4aS,7R,8S)-4,7-Dimethyl-4,4a,5,6,7,8-hexahydro-3H-isochromen-8-yl)-butan-2-one

Downstream raw materials:

artemisinin

C₁₂H₁₃O₂(CH₃)3(O)(OO)

1-oxo-2β-[3-butanone]-3α-methyl-6β-[2-propanol formyl ester]-cyclohexane

(-)-deoxodesoxyartemisinin

Refernces

Synthesis of (+)-Artemisinin and (+)-Deoxoartemisinin from arteannuin B and arteannuic acid

10.1016/S0040-4020(97)10286-1

The research details the first-time synthesis of (+)-Artemisinin and (+)-Deoxoartemisinin from Arteannuin B and Arteannuic Acid. The purpose of this study was to develop a short and efficient synthetic route leveraging prior art for the final photo-oxygenation/cyclization reaction, addressing the urgency in discovering novel antimalarial agents due to the emergence of chloroquine-resistant strains of Plasmodium falciparum. The researchers successfully established a synthetic link between Arteannuin B and Artemisinin, as well as a new route from readily available Arteannuic Acid, utilizing a novel oxidative lactonization reaction and a regioselective protection method. The study concluded that the yields for the photo-oxygenation reaction leading to Artemisinin were comparable to previous syntheses, with no observed "ene" products, likely due to the absence of axial allylic protons in their substrates. The yield for the photo-oxygenation to form Deoxoartemisinin was exceptionally high at 65%, attributed to the enhanced rate of cyclization and the absence of competing ene reactions. Key chemicals used in the process included Arteannuin B, Arteannuic Acid, singlet oxygen, Rose Bengal as a sensitizer, and various reagents for protection and deprotection steps, such as 1,2-bis(trimethylsilyloxy)ethane (BTSE), trimethylsilyltriflate (TMSOTf), and lithium aluminum hydride.