17β-Acetyl-5,6α-epoxy-5α-androstane-3β-ol acetate

Base Information

• Chemical Name: 17β-Acetyl-5,6α-epoxy-5α-androstane-3β-ol acetate
• CAS No.: 14148-09-5
• Molecular Formula: C23H34 O4
• Molecular Weight: 374.521
• Mol file: 14148-09-5.mol

Synonyms:5a-Pregnan-20-one, 5,6a-epoxy-3b-hydroxy-, acetate (6CI,7CI,8CI);5,6-Epoxy-5H-cyclopenta[a]phenanthrene, pregnan-20-one deriv.; 3b-Acetoxy-5,6a-epoxy-5a-pregnan-20-one; 3b-Acetoxy-5a,6a-epoxypregnan-20-one; NSC 20794; NSC 63554

Chemical Property of 17β-Acetyl-5,6α-epoxy-5α-androstane-3β-ol acetate

Chemical Property:

• Vapor Pressure: 5.57E-09mmHg at 25°C
• Boiling Point: 469.3°Cat760mmHg
• Flash Point: 202°C
• PSA: 55.90000
• Density: 1.15g/cm³
• LogP: 4.29730

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 17β-Acetyl-5,6α-epoxy-5α-androstane-3β-ol acetate

There total 13 articles about 17β-Acetyl-5,6α-epoxy-5α-androstane-3β-ol acetate 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: 72.0%

Pregnenolone acetate (1778-02-5) → 3β-acetoxy-5,6β-epoxy-5β-pregnan-20-one (6661-94-5) + 5α,6α-epoxy-20-oxopregnan-3β-yl acetate (14148-09-5)

Guidance literature:

With oxygen; trans-dioxo(5,10,15,20-tetramesitylporphirinato)ruthenium(VI); In benzene; at 20 ℃; for 168h; Title compound not separated from byproducts;

DOI:10.1055/s-1989-27261

Reference yield: 33.1%

Pregnenolone acetate (1778-02-5) → 7-ketopregnenolone acetate (6748-09-0) + Acetic acid (3S,7S,8S,9S,10R,13S,14S,17S)-17-acetyl-7-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester + 3β-acetoxy-5,6β-epoxy-5β-pregnan-20-one (6661-94-5) + 5α,6α-epoxy-20-oxopregnan-3β-yl acetate (14148-09-5)

Guidance literature:

With ferric picolinate complexes; dihydrogen peroxide; In acetonitrile; for 3h; Ambient temperature;

DOI:10.1248/cpb.45.750

Reference yield:

Pregnenolone acetate (1778-02-5) → 7-ketopregnenolone acetate (6748-09-0) + 3β-acetoxy-5,6β-epoxy-5β-pregnan-20-one (6661-94-5) + 5α,6α-epoxy-20-oxopregnan-3β-yl acetate (14148-09-5)

Guidance literature:

With C₂₆H₃₆F₆MnN₆O₆S₂; dihydrogen peroxide; trimethylpyruvic acid; In water; ethyl acetate; acetonitrile; at 20 ℃; for 1h; Reagent/catalyst; diastereoselective reaction;

DOI:10.1021/ol403018x

upstream raw materials:

Pregnenolone acetate

acetic anhydride

3β-hydroxy-5α,6α-epoxypregnane-20-oxide

Pregnenolone

Downstream raw materials:

6β-Phenoxy-5α-hydroxy-pregnan-3,20-dion

6β-Phenoxy-34b,5α-dihydroxy-pregnan-20-on

6α-Fluoro-4-pregnene-3,20-dione

6β-fluoro-5-hydroxy-5α-pregnane-3,20-dione

Refernces

• 1、 Bowers,Ringold. "-". . p. 3710. Retrieved 1959.
• 2、 Salvador,Sa E Melo,Campos Neves. "Oxidations with potassium permanganate - Metal sulphates and nitrates. β-selective epoxidation of Δ5-unsaturated steroids". . p. 687 - 690. Retrieved 1996.
• 3、 Cusso, Olaf,Garcia-Bosch, Isaac,Font, David,Ribas, Xavi,Lloret-Fillol, Julio,Costas, Miquel. "Highly stereoselective epoxidation with H2O2 catalyzed by electron-rich aminopyridine manganese catalysts". supporting information. p. 6158 - 6161. Retrieved 2014/01/17.
• 4、 Kim, Sujeong,Ma, Eunsook. "Synthesis of pregnane derivatives, their cytotoxicity on LNCaP and PC-3 cells, and screening on 5α-reductase inhibitory activity". experimental part. p. 4655 - 4668. Retrieved 2010/04/06.