3,17β-bis(hydroxy)-7α-[6-(4-isoxazol-5-yl-phenyl)-hex-5-ynyl]estra-1,3,5(10)-triene

Base Information

• Chemical Name: 3,17β-bis(hydroxy)-7α-[6-(4-isoxazol-5-yl-phenyl)-hex-5-ynyl]estra-1,3,5(10)-triene
• CAS No.: 1428627-90-0
• Molecular Formula: C₃₃H₃₇NO₃
• Molecular Weight: 495.662
• Mol file: 1428627-90-0.mol

Synonyms:3,17β-bis(hydroxy)-7α-[6-(4-isoxazol-5-yl-phenyl)-hex-5-ynyl]estra-1,3,5(10)-triene

Chemical Property of 3,17β-bis(hydroxy)-7α-[6-(4-isoxazol-5-yl-phenyl)-hex-5-ynyl]estra-1,3,5(10)-triene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,17β-bis(hydroxy)-7α-[6-(4-isoxazol-5-yl-phenyl)-hex-5-ynyl]estra-1,3,5(10)-triene

There total 10 articles about 3,17β-bis(hydroxy)-7α-[6-(4-isoxazol-5-yl-phenyl)-hex-5-ynyl]estra-1,3,5(10)-triene 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: 82.0%

5-(4-iodophenyl)isoxazole (160377-48-0) + 3,17β-bis(hydroxy)-7α-(6-hexynyl)-estra-1,3,5(10)-triene (1428627-88-6) → 3,17β-bis(hydroxy)-7α-[6-(4-isoxazol-5-yl-phenyl)-hex-5-ynyl]estra-1,3,5(10)-triene (1428627-90-0)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at -20 - 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/jm3013773

Reference yield:

3,17β-bis(2-tetrahydropyranyloxy)-7α-(6-hexynyl)-estra-1,3,5(10)-trien-6-one (1428627-86-4) → 3,17β-bis(hydroxy)-7α-[6-(4-isoxazol-5-yl-phenyl)-hex-5-ynyl]estra-1,3,5(10)-triene (1428627-90-0)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogenchloride / tetrahydrofuran; water / 20 °C

2: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 48 h / 20 °C

3: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / N,N-dimethyl-formamide / 24 h / -20 - 20 °C / Inert atmosphere

With hydrogenchloride; triethylsilane; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; boron trifluoride diethyl etherate; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm3013773

Reference yield:

estradiol (50-28-2) → 3,17β-bis(hydroxy)-7α-[6-(4-isoxazol-5-yl-phenyl)-hex-5-ynyl]estra-1,3,5(10)-triene (1428627-90-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: pyridinium p-toluenesulfonate / dichloromethane / Reflux

2.1: lithium diisopropyl amide; potassium tert-butylate / tetrahydrofuran / -78 °C

2.2: 0 °C

3.1: dihydrogen peroxide / water / 25 °C

5.1: potassium tert-butylate / tetrahydrofuran / 0.67 h / 0 °C

5.2: 2 h / -78 - 0 °C

6.1: hydrogenchloride / tetrahydrofuran; water / 20 °C

7.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 48 h / 20 °C

8.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / N,N-dimethyl-formamide / 24 h / -20 - 20 °C / Inert atmosphere

With hydrogenchloride; triethylsilane; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; boron trifluoride diethyl etherate; potassium tert-butylate; dihydrogen peroxide; pyridinium p-toluenesulfonate; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 4.1: |Swern Oxidation;

DOI:10.1021/jm3013773

upstream raw materials:

1-iodo-5-hexyne

3,17β-bis(hydroxy)-7α-(6-hexynyl)-estra-1,3,5(10)-trien-6-one

1-chloro-5-hexyne

5-(4-iodophenyl)isoxazole