(18-Hydroxy-7,11-dimethyl-6-oxo-14-pentacyclo[8.8.0.02,7.03,5.011,16]octadec-16-enyl) 2,2-dimethylpropanoate

Base Information

• Chemical Name: (18-Hydroxy-7,11-dimethyl-6-oxo-14-pentacyclo[8.8.0.02,7.03,5.011,16]octadec-16-enyl) 2,2-dimethylpropanoate
• CAS No.: 82543-09-7
• Molecular Formula: C25H36 O4
• Molecular Weight: 400.558
• European Community (EC) Number: 617-344-8
• Mol file: 82543-09-7.mol

Synonyms:(18-Hydroxy-7,11-dimethyl-6-oxo-14-pentacyclo[8.8.0.02,7.03,5.011,16]octadec-16-enyl) 2,2-dimethylpropanoate;82543-09-7;FT-0669786

Chemical Property of (18-Hydroxy-7,11-dimethyl-6-oxo-14-pentacyclo[8.8.0.02,7.03,5.011,16]octadec-16-enyl) 2,2-dimethylpropanoate

Chemical Property:

• Boiling Point: 515.5±50.0 °C(Predicted)
• PKA: 13.95±0.70(Predicted)
• PSA: 63.60000
• Density: 1.17±0.1 g/cm3(Predicted)
• LogP: 4.30290
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 400.26135963
• Heavy Atom Count: 29
• Complexity: 791

Purity/Quality:

99.9% ^*data from raw suppliers

7β-Hydroxy-15β,16β-methylene-3β-pivaloyloxy-5-androsten-17-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC12CCC(CC1=CC(C3C2CCC4(C3C5CC5C4=O)C)O)OC(=O)C(C)(C)C
• Uses: Drospirenone intermediate.

Technology Process of (18-Hydroxy-7,11-dimethyl-6-oxo-14-pentacyclo[8.8.0.02,7.03,5.011,16]octadec-16-enyl) 2,2-dimethylpropanoate

There total 7 articles about (18-Hydroxy-7,11-dimethyl-6-oxo-14-pentacyclo[8.8.0.02,7.03,5.011,16]octadec-16-enyl) 2,2-dimethylpropanoate 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: 91.0%

trimethylsulfoxonium iodide (1774-47-6) + 7β-hydroxy-3β,15α-dipivaloyloxy-5-androsten-17-one (85390-94-9) → 7β-hydroxy-15β,16β-methylene-3β-pivaloyloxy-5-androsten-17-one (82543-09-7)

Guidance literature:

With sodium hydroxide; In dimethyl sulfoxide; for 1h; Ambient temperature;

Reference yield: 65.0%

2,2-dimethylpropanoic anhydride (1538-75-6) + 3β,7β-dihydroxy-15β,16β-methylene-5-androsten-17-one (82543-07-5) → 7β-hydroxy-15β,16β-methylene-3β-pivaloyloxy-5-androsten-17-one (82543-09-7)

Guidance literature:

With dmap; In pyridine; for 72h; Ambient temperature;

Reference yield:

dehydroepiandrosterone (53-43-0) → 7β-hydroxy-15β,16β-methylene-3β-pivaloyloxy-5-androsten-17-one (82543-09-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / Colletotrichum lini / 36 h

2: 97 percent / 35 percent HClO₄ / various solvent(s) / 4 h / Ambient temperature

3: 90 percent / 4-dimethylaminopyridine / pyridine / 4 h / 50 °C

4: 91 percent / NaOH / dimethylsulfoxide / 1 h / Ambient temperature

With dmap; sodium hydroxide; perchloric acid; Colletotrichum lini; In pyridine; dimethyl sulfoxide;

upstream raw materials:

trimethylsulfoxonium iodide

7β-hydroxy-3β,15α-dipivaloyloxy-5-androsten-17-one

2,2-dimethylpropanoic anhydride

3β,7β-dihydroxy-15β,16β-methylene-5-androsten-17-one

Downstream raw materials:

5,6β-epoxy-7β-hydroxy-15β,16β-methylene-3β-pivaloyloxy-5β-androstan-17-one

7α-chloro-5,6β-epoxy-15β,16β-methylene-3β-pivaloyloxy-5β-androstan-17-one

5-hydroxy-15β,16β-methylene-3β-pivaloyloxy-5β-androst-6-en-17-one

Spirorenone

Refernces

• 1、 -. "Process for preparing 3β,7β-dihydroxy-Δ5 -steroids". . . Retrieved 2008/06/13.