Artemisone

Base Information

• Chemical Name: Artemisone
• CAS No.: 255730-18-8
• Molecular Formula: C₁₉H₃₁NO₆S
• Molecular Weight: 401.524
• Hs Code.: 9999999999
• UNII: 796LMW5BUZ
• ChEMBL ID: CHEMBL516268
• Metabolomics Workbench ID: 144823
• NCI Thesaurus Code: C87431
• Nikkaji Number: J2.302.887E
• Wikidata: Q27266724
• Mol file: 255730-18-8.mol

Synonyms:artemisone;BAY 44-9585

Chemical Property of Artemisone

Chemical Property:

• Boiling Point: 536.5±50.0 °C(Predicted)
• PKA: 2.99±0.20(Predicted)
• PSA: 82.68000
• Density: 1.33±0.1 g/cm3(Predicted)
• LogP: 2.59590
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 401.18720888
• Heavy Atom Count: 27
• Complexity: 696

Purity/Quality:

97% ^*data from raw suppliers

Artemisone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2C(C(OC3C24C1CCC(O3)(OO4)C)N5CCS(=O)(=O)CC5)C
• Isomeric SMILES: C[C@@H]1CC[C@H]2[C@H]([C@@H](O[C@H]3[C@@]24[C@H]1CC[C@](O3)(OO4)C)N5CCS(=O)(=O)CC5)C

Technology Process of Artemisone

There total 9 articles about Artemisone 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: 100.0%

artemiside (255730-17-7) → 4-[(3R,5aS,6R,8aS,9R,10R,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl]thiomorpholine 1,1-dioxide (255730-18-8)

Guidance literature:

With tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide; In dichloromethane; at 20 ℃;

DOI:10.1002/anie.200503071

Reference yield:

thiomorpholine 1,1-dioxide (39093-93-1) + C15H23BrO4 (887195-43-9) → 4-[(3R,5aS,6R,8aS,9R,10R,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl]thiomorpholine 1,1-dioxide (255730-18-8)

Guidance literature:

With triethylamine; In toluene; at 0 - 22 ℃; for 3h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;

DOI:10.1016/j.tet.2018.04.027

Reference yield:

thiomorpholine 1,1-dioxide (39093-93-1) + 10-chloroartemisinin → 4-[(3R,5aS,6R,8aS,9R,10R,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl]thiomorpholine 1,1-dioxide (255730-18-8) + 9,10-dehydrodihydroartemisinin (82596-30-3)

Guidance literature:

With triethylamine; In toluene; at 0 - 22 ℃; for 1.75h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;

DOI:10.1016/j.tet.2018.04.027

upstream raw materials:

artemiside

dihydroartemisinin

10α-(trimethylsilyloxy)dihydroartemisinin

C₁₅H₂₃BrO₄

Downstream raw materials:

(2S, 3R, 6S)-2-(3-oxobutyl)-3-methyl-6-<(R)2-propanal>-cyclohexanone

β-2-deoxy-9-epidihydroartemisinin

deoxydihydroqinghaosu

Refernces

• 1、 Chan, Wing Chi,Wai Chan, Dennis Ho,Lee, Kin Wo,Tin, Wing Shan,Wong, Ho Ning,Haynes, Richard K.. "Evaluation and optimization of synthetic routes from dihydroartemisinin to the alkylamino-artemisinins artemiside and artemisone: A test of N-glycosylation methodologies on a lipophilic peroxide". . p. 5156 - 5171. Retrieved 2018.