Androst-16-en-3-ol, 17-(3-pyridinyl)-, acetate (ester),(3β,5α)-

Base Information

• Chemical Name: Androst-16-en-3-ol, 17-(3-pyridinyl)-, acetate (ester),(3β,5α)-
• CAS No.: 219843-76-2
• Molecular Formula: C26H35NO2
• Molecular Weight: 393.5616
• Mol file: 219843-76-2.mol

Synonyms:Androst-16-en-3-ol, 17-(3-pyridinyl)-, acetate (ester),(3β,5α)-

Chemical Property of Androst-16-en-3-ol, 17-(3-pyridinyl)-, acetate (ester),(3β,5α)-

Chemical Property:

• Melting Point: 152 - 153 °C
• PSA: 39.19000
• LogP: 6.04930

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

5,6-DihydroabirateroneAcetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 5,6-Dihydroabiraterone Acetate is used in the preparation and activity of abirateron metabolites, redirecting abiraterone metabolite to fine-tune prostate cancer anti-androgen therapy.

Technology Process of Androst-16-en-3-ol, 17-(3-pyridinyl)-, acetate (ester),(3β,5α)-

There total 8 articles about Androst-16-en-3-ol, 17-(3-pyridinyl)-, acetate (ester),(3β,5α)- 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: 90.0%

3β-acetoxy-5α-androsta-16-ene-17-yl trifluoromethanesulfonate (91934-55-3) + 3-Diethylboranylpyridine (89878-14-8) → 3β-acetyloxy-17-(3-pyridinyl)-5α-androst-16-ene (219843-76-2)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In tetrahydrofuran; at 80 ℃; for 1h;

DOI:10.1021/jm981017j

Reference yield: 80.0%

3-Bromopyridine (626-55-1,163928-56-1) + 3β-acetyloxy-17-(4’,4’,5’,5’-tetramethyl-1’,3’,2’-dioxaborolan-2-yl)-5α-androst-16-ene → 3β-acetyloxy-17-(3-pyridinyl)-5α-androst-16-ene (219843-76-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In methanol; water; benzene; for 24h; Schlenk technique; Reflux;

DOI:10.1002/adsc.201601289

Reference yield:

acetic anhydride (108-24-7) + (3β,5α)-17-(3'-pyridinyl)androst-16-en-3-ol (219843-75-1,1940176-03-3) → 3β-acetyloxy-17-(3-pyridinyl)-5α-androst-16-ene (219843-76-2)

Guidance literature:

With pyridine; In toluene; for 4h; Reflux;

upstream raw materials:

3β-acetoxy-5α-androsta-16-ene-17-yl trifluoromethanesulfonate

3-Diethylboranylpyridine

Epiandrosterone

3β-acetoxy-5α-androstan-17-one

Downstream raw materials:

17-(3-pyridyl)-5α-androsta-16-ene-3α-ol

17-(3-pyridyl)-5α-androsta-16-ene-3-one

(3β,5α)-17-(3'-pyridinyl)androst-16-en-3-ol

Refernces

• 1、 -. "Abiraterone acetate reducing impurity and preparation method thereof". . . Retrieved 2017/10/22.
• 2、 Jarman,Barrie,Llera. "The 16,17-double bond is needed for irreversible inhibition of human cytochrome P45017α by abiraterone (17-(3-pyridyl)androsta-5,16-dien-3β- ol) and related steroidal inhibitors". . p. 5375 - 5381. Retrieved 2007/10/03.