alpha-Arteether

Base Information

• Chemical Name: alpha-Arteether
• CAS No.: 82534-75-6
• Molecular Formula: C17H28O5
• Molecular Weight: 312.406
• UNII: R6TF0B136Q
• DSSTox Substance ID: DTXSID50231827
• Nikkaji Number: J414.140G
• Wikidata: Q27287865
• ChEMBL ID: CHEMBL345679
• Mol file: 82534-75-6.mol

Synonyms:alpha-arteether;82534-75-6;3,12-Epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin, 10-ethoxydecahydro-3,6,9-trimethyl-, (3R,5aS,6R,8aS,9R,10R,12R,12aR)-;UNII-R6TF0B136Q;R6TF0B136Q;(1R,4S,5R,8S,9R,10R,12R,13R)-10-ethoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecane;.ALPHA.-ARTEETHER;CHEMBL345679;DTXSID50231827;Q27287865;3,12-EPOXY-12H-PYRANO(4,3-J)-1,2-BENZODIOXEPIN, 10-ETHOXYDECAHYDRO-3,6,9-TRIMETHYL-, (3R-(3.ALPHA.,5A.BETA.,6.BETA.,8A.BETA.,9.ALPHA.,10.BETA.,12.BETA.,12AR*))-

Chemical Property of alpha-Arteether

Chemical Property:

• Vapor Pressure: 2.06E-05mmHg at 25°C
• Refractive Index: 1.516
• Boiling Point: 372.4 °C at 760 mmHg
• Flash Point: 146 °C
• PSA: 46.15000
• Density: 1.16 g/cm³
• LogP: 3.23090
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 312.19367399
• Heavy Atom Count: 22
• Complexity: 443

Purity/Quality:

99% ^*data from raw suppliers

α-Arteether ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1C(C2CCC(C3C24C(O1)OC(CC3)(OO4)C)C)C
• Isomeric SMILES: CCO[C@H]1[C@@H]([C@@H]2CC[C@H]([C@H]3[C@]24[C@H](O1)O[C@@](CC3)(OO4)C)C)C
• Uses: The diastereomer of Arteether, a potent antimalarial drug.

Technology Process of alpha-Arteether

There total 7 articles about alpha-Arteether 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: 72.0%

ethanol (64-17-5) + dihydroartemisinin (71939-50-9) → Alpha-Arteether (82534-75-6) + artemotil (75887-54-6)

Guidance literature:

With boron trifluoride diethyl etherate; In benzene; for 1h; Heating;

DOI:10.1021/jm00398a026

Reference yield:

ethanol (64-17-5) + dihydroartemisinin (71939-50-9) → Alpha-Arteether (82534-75-6) + artemotil (75887-54-6)

Guidance literature:

With boron trifluoride diethyl etherate;

Reference yield:

ethanol (64-17-5) + C12H13O2(CH3)3(O)(OO) (63968-64-9) → Alpha-Arteether (82534-75-6) + artemotil (75887-54-6)

Guidance literature:

With Trimethyl orthoacetate; sodium tetrahydroborate; cellulose sulfuric acid; In tetrahydrofuran; at -5 - 20 ℃; for 2.5h; Reagent/catalyst; Overall yield = 82 %;

DOI:10.1039/c4ra05531d

upstream raw materials:

ethanol

dihydroartemisinin

dihydroartemisinin

artemotil

Downstream raw materials:

(R)-2-((1S,4R)-4-Methyl-7-oxo-1,2,3,4,4a,5,6,7-octahydro-naphthalen-1-yl)-propionaldehyde

Refernces

• 1、 Bora, Pranjal P.,Baruah, Nabajyoti,Bez, Ghanashyam,Barua, Nabin C.. "New method for the synthesis of ether derivatives of artemisinin". experimental part. p. 1218 - 1225. Retrieved 2012/04/04.
• 2、 -. "SINGLE POT CONVERSION OF ARTEMISININ INTO ARTEETHER". Page 7. . Retrieved 2008/06/13.