3α-Hydroxydesoxy ArteMether

Base Information

• Chemical Name: 3α-Hydroxydesoxy ArteMether
• CAS No.: 174097-70-2
• Molecular Formula: C₁₆H₂₆O₅
• Molecular Weight: 298.379
• Mol file: 174097-70-2.mol

Synonyms:3α-Hydroxydesoxy ArteMether;(2S,3R,3aS,6R,6aS,8R,9S,10aR,10bR)-Decahydro-2-Methoxy-3,6,9-triMethyl-10aH-9,10b-epoxypyrano[4,3,2-jk][2]benzoxepin-8-ol;[2S-(2α,3α,3aβ,6β,6aβ,8β,9β,10aα,10bβ)]-Decahydro-2-Methoxy-3,6,9-triMethyl-10aH-9,10b-Epoxypyrano[4,3,2-jk][2]benzoxepin-8-ol;3α-HydroxydeoxyarteMether

Chemical Property of 3α-Hydroxydesoxy ArteMether

Chemical Property:

• Boiling Point: 403.9±45.0 °C(Predicted)
• PKA: 13.61±0.70(Predicted)
• PSA: 57.15000
• Density: 1.22±0.1 g/cm3(Predicted)
• LogP: 1.88000

Purity/Quality:

> 95% ^*data from raw suppliers

3α-HydroxydesoxyArtemether ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A metabolite of Artemether (A777400) and derivative of the antimalarial drug Artemisinin (A777500). Studies suggest that it may display neurotoxicity in animals due to its interaction with iron.

Technology Process of 3α-Hydroxydesoxy ArteMether

There total 3 articles about 3α-Hydroxydesoxy ArteMether 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: 44.0%

artemether (71963-77-4) → 9α-acetoxy-10β-methoxyartemethin-I (181528-64-3) + 3α-hydroxydeoxydihydroqinghaosu + 3α-hydroxy-12β-methoxyartemethin-III (174097-70-2)

Guidance literature:

With iron(II) sulfate; In water; acetonitrile; at 37 ℃;

DOI:10.1021/ja973080o

Reference yield: 10.0%

DL-cysteine hydrochloride (10318-18-0) + artemether (71963-77-4) → 9α-acetoxy-10β-methoxyartemethin-I (181528-64-3) + 3α-hydroxy-12β-methoxyartemethin-III (174097-70-2) + Acetic acid (1R,3S,4R,4aS,7R,8S,8aR)-8-ethyl-8a-hydroxy-3-methoxy-4,7-dimethyl-octahydro-isochromen-1-yl ester + 3-[2-((1R,3S,4R,4aS,7R,8S,8aR)-1-Acetoxy-8a-hydroxy-3-methoxy-4,7-dimethyl-octahydro-isochromen-8-yl)-ethylsulfanyl]-2-amino-propionic acid

Guidance literature:

With sodium hydrogencarbonate; iron(II) sulfate; In acetonitrile; at 20 ℃; for 4h; Further byproducts given;

DOI:10.1016/S0960-894X(03)00293-2

Reference yield:

artemether (71963-77-4) → 9α-acetoxy-10β-methoxyartemethin-I (181528-64-3) + 3α-hydroxy-12β-methoxyartemethin-III (174097-70-2)

Guidance literature:

With oxygen; methylene blue; ascorbic acid; In acetonitrile; at 20 ℃; for 24h; pH=7.4; aq. phosphate buffer;

DOI:10.1002/cmdc.201000225

upstream raw materials:

artemether

DL-cysteine hydrochloride

Refernces

• 1、 Wu, Wen-Min,Wu, Yikang,Wu, Yu-Lin,Yao, Zhu-Jun,Zhou, Cheng-Ming,Li, Ying,Shan, Feng. "Unified mechanistic framework for the Fe(II)-induced cleavage of Qinghaosu and derivatives/analogues. The first spin-trapping evidence for the previously postulated secondary C-4 radical". . p. 3316 - 3325. Retrieved 1998.