(1R,4S,5R,12S,13R)-1,5-Dimethyl-9-methylidene-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one

Base Information

• Chemical Name: (1R,4S,5R,12S,13R)-1,5-Dimethyl-9-methylidene-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one
• CAS No.: 101020-89-7
• Molecular Formula: C15H20 O5
• Molecular Weight: 280.321
• DSSTox Substance ID: DTXSID20905902
• Mol file: 101020-89-7.mol

Synonyms:artemisitene

Chemical Property of (1R,4S,5R,12S,13R)-1,5-Dimethyl-9-methylidene-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one

Chemical Property:

• Vapor Pressure: 3.52E-07mmHg at 25°C
• Boiling Point: 417.5°Cat760mmHg
• Flash Point: 185.9°C
• PSA: 53.99000
• Density: 1.26g/cm³
• LogP: 2.31500
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 280.13107373
• Heavy Atom Count: 20
• Complexity: 489

Purity/Quality:

97% ^*data from raw suppliers

Artemisitene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2C(=C)C(=O)OC3C24C1CCC(O3)(OO4)C
• Isomeric SMILES: C[C@@H]1CCC2C(=C)C(=O)O[C@H]3[C@@]24[C@H]1CC[C@](O3)(OO4)C
• Uses: Artemisitene, the oxidized form of Artemisinin (A777500), exists as a minor constituent in an American variant of Artemisia annua. Artemisinin precursors are the important basic substances for biosynthesis of Artemisinin, including Artemisinic acid, Artemisinin B, Artemisitene, etc. An antimalarial agent.

Technology Process of (1R,4S,5R,12S,13R)-1,5-Dimethyl-9-methylidene-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one

There total 10 articles about (1R,4S,5R,12S,13R)-1,5-Dimethyl-9-methylidene-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one 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: 88.0%

C15H22O6 (127867-59-8) → dehydroqinghaosu (101020-89-7) + (4aS,7R,8S,8aR)-3-Hydroxy-7-methyl-4-methylene-8-(3-oxo-butyl)-hexahydro-benzo[c][1,2]dioxine-8a-carbaldehyde

Guidance literature:

With pyridine; acetic anhydride; at 20 ℃; for 0.833333h;

DOI:10.1039/b104471k

Reference yield: 78.0%

(+)-octahydro-3,6α-dimethyl-3,12-epoxy-9β-(phenylthio)-12H-pyrano[4,3j]-1,2-benzodioxepin-10(3H)-one → dehydroqinghaosu (101020-89-7)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 ℃; for 6h; Product distribution / selectivity;

Reference yield: 78.0%

(+)-octahydro-3,6α-dimethyl-3,12-epoxy-9β-(phenylthio)-12H-pyrano[4,3j]-1,2-benzodioxepin-10(3H)-one (467223-78-5) → dehydroqinghaosu (101020-89-7)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 ℃; for 6h;

DOI:10.1021/jm020142z

upstream raw materials:

artemisinic acid

methyl <1'R,2'S,5'R,6'S>-2-<1'-formyl-1'-hydroperoxy-5'-methyl-6'-(3''-oxobutyl)cyclohex-2'-yl>propenoate

C₁₂H₁₃O₂(CH₃)3(O)(OO)

C₁₅H₂₂O₆

Downstream raw materials:

C₁₂H₁₃O₂(CH₃)3(O)(OO)

(+)-9-isoartemisinin

2-((1R,4R,4aS)-4-Methyl-7-oxo-1,2,3,4,4a,5,6,7-octahydro-naphthalen-1-yl)-acrylic acid methyl ester