(17Z)-15β-(4-benzoyloxybutyl)-2β,3β-isopropylidenedioxy-6,6-ethylenedioxy-5α-pregna-17-ene

Base Information

• Chemical Name: (17Z)-15β-(4-benzoyloxybutyl)-2β,3β-isopropylidenedioxy-6,6-ethylenedioxy-5α-pregna-17-ene
• CAS No.: 1353113-35-5
• Molecular Formula: C₃₇H₅₂O₆
• Molecular Weight: 592.816
• Mol file: 1353113-35-5.mol

Synonyms:(17Z)-15β-(4-benzoyloxybutyl)-2β,3β-isopropylidenedioxy-6,6-ethylenedioxy-5α-pregna-17-ene

Chemical Property of (17Z)-15β-(4-benzoyloxybutyl)-2β,3β-isopropylidenedioxy-6,6-ethylenedioxy-5α-pregna-17-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (17Z)-15β-(4-benzoyloxybutyl)-2β,3β-isopropylidenedioxy-6,6-ethylenedioxy-5α-pregna-17-ene

There total 3 articles about (17Z)-15β-(4-benzoyloxybutyl)-2β,3β-isopropylidenedioxy-6,6-ethylenedioxy-5α-pregna-17-ene 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: 92.0%

(17Z)-15β-(4-(dimethyl-tert-butylsilyloxy)butyl)-2β,3β-isopropylidenedioxy-6,6-ethylenedioxy-5α-pregna-17-ene (1353113-31-1) + benzoyl chloride (98-88-4) → (17Z)-15β-(4-benzoyloxybutyl)-2β,3β-isopropylidenedioxy-6,6-ethylenedioxy-5α-pregna-17-ene (1353113-35-5)

Guidance literature:

(17Z)-15β-(4-(dimethyl-tert-butylsilyloxy)butyl)-2β,3β-isopropylidenedioxy-6,6-ethylenedioxy-5α-pregna-17-ene; With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2h; Inert atmosphere;

benzoyl chloride; With pyridine; In dichloromethane; for 2.5h; Inert atmosphere;

DOI:10.1134/S1070363211100185

Reference yield:

2β,3β-isopropylidenedioxy-6,6-ethylenedioxy-5α-androst-15-en-17-one → (17Z)-15β-(4-benzoyloxybutyl)-2β,3β-isopropylidenedioxy-6,6-ethylenedioxy-5α-pregna-17-ene (1353113-35-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.08 h / -20 °C / Inert atmosphere

1.2: 0.17 h / -78 °C / Inert atmosphere

2.1: benzene / 2.5 h / Inert atmosphere; Reflux

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / Inert atmosphere

3.2: 2.5 h / Inert atmosphere

With copper(I) bromide dimethylsulfide complex; tetrabutyl ammonium fluoride; In tetrahydrofuran; benzene; 1.1: Michael condensation;

DOI:10.1134/S1070363211100185

Reference yield:

15β-(4-(dimethyl-tert-butylsilyloxy)butyl)-2β,3β-isopropylidenedihydroxy-6,6-ethylenedioxy-5α-androstan-17-one (1353113-27-5) → (17Z)-15β-(4-benzoyloxybutyl)-2β,3β-isopropylidenedioxy-6,6-ethylenedioxy-5α-pregna-17-ene (1353113-35-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: benzene / 2.5 h / Inert atmosphere; Reflux

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / Inert atmosphere

2.2: 2.5 h / Inert atmosphere

With tetrabutyl ammonium fluoride; In tetrahydrofuran; benzene;

DOI:10.1134/S1070363211100185

upstream raw materials:

15β-(4-(dimethyl-tert-butylsilyloxy)butyl)-2β,3β-isopropylidenedihydroxy-6,6-ethylenedioxy-5α-androstan-17-one

(17Z)-15β-(4-(dimethyl-tert-butylsilyloxy)butyl)-2β,3β-isopropylidenedioxy-6,6-ethylenedioxy-5α-pregna-17-ene

benzoyl chloride

Downstream raw materials:

(20S)-15β-(4-benzoyloxybutyl)-20-hydroxymethyl-2β,3β-isopropylidenedihydroxy-6,6-ethylenedioxy-5α-pregna-16-ene