Deoxy Artemisinin

Base Information

• Chemical Name: Deoxy Artemisinin
• CAS No.: 72826-63-2
• Molecular Formula: C15H22 O4
• Molecular Weight: 266.337
• Mol file: 72826-63-2.mol

Synonyms:10aH-9,10b-Epoxypyrano[4,3,2-jk][2]benzoxepin-2(3H)-one,octahydro-3,6,9-trimethyl-, [3R-(3a,3ab,6b,6ab,9b,10aa,10bb)]-; Deoxyarteannuin; Deoxyartemisinin; Deoxyqinghaosu; Desoxyartemisinin;Hydroarteannuin; Qing Hau Sau III; Qinghaosu III

Chemical Property of Deoxy Artemisinin

Chemical Property:

• Vapor Pressure: 1.59E-08mmHg at 25°C
• Melting Point: 104-106°C
• Boiling Point: 412.4°C at 760 mmHg
• Flash Point: 151.4°C
• PSA: 44.76000
• Density: 1.12g/cm³
• LogP: 2.46330
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

Purity/Quality:

98%min ^*data from raw suppliers

Deoxy Artemisinin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An analogue of Artemisinin, an antimalarial agent. An analogue of Artemisinin, an antimalarial agent

Technology Process of Deoxy Artemisinin

There total 13 articles about Deoxy Artemisinin 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: 30.0%

(1S,6R,9S,12S)-9-Benzyl-12-methoxy-10,11,13-trioxa-tricyclo[7.2.2.01,6]tridecane → 2-deoxyartemisinin (72826-63-2) + (3R,3aS,6R,6aS,8R,9S,10aS,10bR)-octahydro-8-hydroxy-3,6,9-trimethyl-10aH-9,10b-epoxypyrano[4,3,2-jk][2]benzoxepin-2(3H)-one (82003-85-8) + (4aR,8aS)-2-Oxo-octahydro-chromene-8a-carbaldehyde

Guidance literature:

With iron(II) bromide; In tetrahydrofuran; Yields of byproduct given; Ambient temperature;

DOI:10.1021/ja00126a042

Reference yield: 30.0%

(1S,6R,9S,12S)-9-Biphenyl-4-ylmethyl-12-methoxy-10,11,13-trioxa-tricyclo[7.2.2.01,6]tridecane → 2-deoxyartemisinin (72826-63-2) + (3R,3aS,6R,6aS,8R,9S,10aS,10bR)-octahydro-8-hydroxy-3,6,9-trimethyl-10aH-9,10b-epoxypyrano[4,3,2-jk][2]benzoxepin-2(3H)-one (82003-85-8) + (4aR,8aS)-2-Oxo-octahydro-chromene-8a-carbaldehyde

Guidance literature:

With iron(II) bromide; In tetrahydrofuran; Yields of byproduct given; Ambient temperature;

DOI:10.1021/ja00126a042

Reference yield:

(2R,1'S,3'S,4'S)-2-<4'-methyl-3'-(3''-oxobutyl)-2'(E)-<(trimethylsilyl)methylene>cyclohexyl>propionic acid (116399-93-0) → C12H13O2(CH3)3(O)(OO) (63968-64-9) + 2-deoxyartemisinin (72826-63-2)

Guidance literature:

With oxygen; ozone; trifluoroacetic acid; Yield given. Multistep reaction. Yields of byproduct given; 1.) CH₂Cl₂, -78 deg C, 2.) CDCl₃;

DOI:10.1021/ja00029a028

upstream raw materials:

dihydroartemisinin

(2R,1'S,3'S,4'S)-2-<4'-methyl-3'-(3''-oxobutyl)-2'(E)-<(trimethylsilyl)methylene>cyclohexyl>propionic acid

2,5,5-trimethyl-2-<2'-<4''-(1(S)-carboxyethyl)-1''(R)-methyl-3''-<(trimethylsilyl)methylene>cyclohex-2''-yl>ethyl>-1,3-dioxane

C₁₂H₁₃O₂(CH₃)3(O)(OO)

Refernces

• 1、 Wu, Yikang,Liu, He-Hua. "Cleavage of qinghaosu (artemisinin) induced by non-iron transition-metal ions in the presence of excess cysteine". . p. 3074 - 3080. Retrieved 2003.
• 2、 Posner, Gary H.,Cumming, Jared N.,Ploypradith, Poonsakdi,Oh, Chang Ho. "Evidence for Fe(IV)=O in the molecular mechanism of action of the trioxane antimalarial artemisinin". . p. 5885 - 5886. Retrieved 1995.
• 3、 Sy, Lai-King,Brown, Geoffrey D. "The role of the 12-carboxylic acid group in the spontaneous autoxidation of dihydroartemisinic acid". . p. 909 - 923. Retrieved 2007/10/03.