anhydrodihydroartemisinin

Base Information

• Chemical Name: anhydrodihydroartemisinin
• CAS No.: 82596-30-3
• Molecular Formula: C15H22O4
• Molecular Weight: 266.337
• Mol file: 82596-30-3.mol

Synonyms:anhydrodihydroartemisinin;(+)-9,10-AnhydrodehydroarteMisinin;(3R,5aS,6R,8aS,12R,12aR)-3,4,5,5a,6,7,8,8a-Octahydro-3,6,9-triMethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin;9,10-Anhydro-10-deoxoarteMisinin;9,10-AnhydrodehydroarteMisinin;Anhydrod

Chemical Property of anhydrodihydroartemisinin

Chemical Property:

• PSA: 36.92000
• LogP: 3.13600
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

AnhydroDihydroArtemisinin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Anhydrodihydroartemisinin is a semisynthetic derivative of Artersiminin (A777500). Anhydrodihydroartemisinin is a decomposition product of Artesunate (A777800) and Dihydroartemisinin (D448360). Anhydrodihydroartemisinin showed antimalarial activity although much weaker than its parent compound.

Technology Process of anhydrodihydroartemisinin

There total 12 articles about anhydrodihydroartemisinin 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%

1,2,3-trimethoxybenzene (621-23-8) + (5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-trimethyldecahydro-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl benzoate (163381-14-4) → 9,10-dehydrodihydroartemisinin (82596-30-3) + bis(3,6,9-trimethyl-3,12-epidioxy-3,4,5,5a,6,7,8,8a,9,10-decahydro-12H-pyrano[4,3-j][1,2]benzodioxepin-10-yl) ether (150358-71-7) + 10α-(2',4',6'-trimethoxyphenyl)-10-deoxo-10-dihydroartemisinin

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -30 ℃; for 1h;

DOI:10.1002/ejoc.200300064

Reference yield: 70.0%

Methyl (R)-3-hydroxybutyrate (3976-69-0) + dihydroartemisinin (71939-50-9) → 9,10-dehydrodihydroartemisinin (82596-30-3) + artemether (71963-77-4) + C20H32O7 (120020-67-9)

Guidance literature:

With boron trifluoride diethyl etherate; In diethyl ether; for 24h; Ambient temperature;

DOI:10.1021/jm00126a017

Reference yield: 59.0%

p-hydroxyphenethyl alcohol (501-94-0) + dihydroartemisinin (71939-50-9) → C23H32O6 + 9,10-dehydrodihydroartemisinin (82596-30-3)

Guidance literature:

With boron trifluoride diethyl etherate; In diethyl ether; at 0 ℃; for 1h; diastereoselective reaction; Inert atmosphere;

DOI:10.1002/cmdc.202100196

upstream raw materials:

(S)-3-hydroxybutyric acid methyl ester

dihydroartemisinin

Methyl (R)-3-hydroxybutyrate

dihydroartemisinin acetate

Downstream raw materials:

artemotil

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

Refernces

• 1、 Chorki,Grellepois,Crousse,Ourevitch,Bonnet-Delpon,Begue. "Fluoro artemisinins: Difluoromethylene ketones". . p. 7858 - 7863. Retrieved 2001.
• 2、 Fan, Xiaolei,Sans, Victor,Yaseneva, Polina,Plaza, Dorota D.,Williams, Jonathan,Lapkin, Alexei. "Facile stoichiometric reductions in flow: An example of artemisinin". experimental part. p. 1039 - 1042. Retrieved 2012/08/07.