1,3,5(10)-ESTRATRIEN-17-ALPHA-METHYL-3,17-BETA-DIOL 3-METHYL ETHER

Base Information

• Chemical Name: 1,3,5(10)-ESTRATRIEN-17-ALPHA-METHYL-3,17-BETA-DIOL 3-METHYL ETHER
• CAS No.: 4954-14-7
• Molecular Formula: C20H28 O2
• Molecular Weight: 300.441
• Mol file: 4954-14-7.mol

Synonyms:Estra-1,3,5(10)-triene,3,17b-dimethoxy- (6CI,7CI,8CI); 17b-Dimethylestradiol; 3,17b-Dimethoxyestra-1,3,5(10)-triene;Estradiol dimethyl ether; Methylestradiol methyl ether

Chemical Property of 1,3,5(10)-ESTRATRIEN-17-ALPHA-METHYL-3,17-BETA-DIOL 3-METHYL ETHER

Chemical Property:

• Melting Point: 160.5-162 °C(Solv: ethanol (64-17-5))
• Boiling Point: 410.0±45.0 °C(Predicted)
• PSA: 29.46000
• Density: 1.08±0.1 g/cm3(Predicted)
• LogP: 4.30230
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), DMSO (Slightly, Heated), Ethanol (Slightly), Ethyl Acetat

Purity/Quality:

99% ^*data from raw suppliers

17β-EstradiolDimethylEther ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 17β-Estradiol (E888000) derivative, a hormone secreted by premenopausal ovaries.

Technology Process of 1,3,5(10)-ESTRATRIEN-17-ALPHA-METHYL-3,17-BETA-DIOL 3-METHYL ETHER

There total 9 articles about 1,3,5(10)-ESTRATRIEN-17-ALPHA-METHYL-3,17-BETA-DIOL 3-METHYL ETHER 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: 83.0%

estradiol (50-28-2) + methyl iodide (74-88-4) → (8R,9S,13S,14S,17S)-3,17-dimethoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene (4954-14-7)

Guidance literature:

estradiol; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.25h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/ol101154h

Reference yield:

Estrone (53-16-7) → (8R,9S,13S,14S,17S)-3,17-dimethoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene (4954-14-7)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂, HCl / PtO₂

2: aq. NaOH / ethanol

With hydrogenchloride; sodium hydroxide; hydrogen; platinum(IV) oxide; In ethanol;

DOI:10.1016/0039-128X(65)90103-0

Reference yield:

methanol (67-56-1) + estrone 3-methyl ether (1624-62-0) → (8R,9S,13S,14S,17S)-3,17-dimethoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene (4954-14-7)

Guidance literature:

With hydrogenchloride; hydrogen; platinum(IV) oxide;

DOI:10.1016/0039-128X(65)90103-0

upstream raw materials:

3-O-methyl-17β-oestradiol

estrone 3-methyl ether

estradiol

methyl iodide

Downstream raw materials:

7α-benzylthio-3,17β-bis(methoxy)estra-1,3,5(10)-triene

17-β-estradiol 17-acetate

3-O-methyl-17β-oestradiol

estradiol

Refernces

• 1、 Xia, Anjie,Qi, Xueyu,Mao, Xin,Wu, Xiaoai,Yang, Xin,Zhang, Rong,Xiang, Zhiyu,Lian, Zhong,Chen, Yingchun,Yang, Shengyong. "Metal-Free Aerobic Oxidative Selective C-C Bond Cleavage in Heteroaryl-Containing Primary and Secondary Alcohols". supporting information. . Retrieved 2019/05/07.
• 2、 Liu, Jing-Hui,Yang, Chu-Ting,Lu, Xiao-Yu,Zhang, Zhen-Qi,Xu, Ling,Cui, Mian,Lu, Xi,Xiao, Bin,Fu, Yao,Liu, Lei. "Copper-Catalyzed Reductive Cross-Coupling of Nonactivated Alkyl Tosylates and Mesylates with Alkyl and Aryl Bromides". supporting information. p. 15334 - 15338. Retrieved 2016/02/18.