13-Methyl-17-(oxan-2-yloxy)-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-ol

Base Information

• Chemical Name: 13-Methyl-17-(oxan-2-yloxy)-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-ol
• CAS No.: 3589-90-0
• Molecular Formula: C23H32O3
• Molecular Weight: 356.505
• NSC Number: 99694
• Mol file: 3589-90-0.mol

Synonyms:17 beta-estradiol 3-tetrahydropyranyl ether

Chemical Property of 13-Methyl-17-(oxan-2-yloxy)-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-ol

Chemical Property:

• Vapor Pressure: 5.64E-11mmHg at 25°C
• Boiling Point: 508.8°Cat760mmHg
• Flash Point: 261.5°C
• PSA: 38.69000
• Density: 1.16g/cm³
• LogP: 5.16010
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 356.23514488
• Heavy Atom Count: 26
• Complexity: 508

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2OC4CCCCO4)CCC5=C3C=CC(=C5)O

Technology Process of 13-Methyl-17-(oxan-2-yloxy)-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-ol

There total 15 articles about 13-Methyl-17-(oxan-2-yloxy)-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-ol 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: 50.0%

3,17β-bis(2-tetrahydropyranyloxy)estra-1,3,5(10)-triene (3589-91-1) → estradiol 17β-tetrahydropyranyl ether (3589-90-0)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 25 ℃; for 1h;

DOI:10.1016/0039-128X(90)90018-7

Reference yield: 15.0%

3-O-(tert-butyldimethylsilyl)-17β-O'-(tetrahydropyranyl)-19-oxoandrosta-2,4-diene-3,17β-diol (112506-37-3) → estradiol 17β-tetrahydropyranyl ether (3589-90-0) + 3-O-(tert-butyldimethylsilyl)-17β-O'-(tetrahydropyranyl)estradiol (112506-38-4)

Guidance literature:

With potassium hydroxide; dihydrogen peroxide; In methanol; dichloromethane; at 4 ℃; for 4h;

DOI:10.1021/ja00021a044

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → estradiol 17β-tetrahydropyranyl ether (3589-90-0)

Guidance literature:

Multi-step reaction with 3 steps

1: POCl₃ / 3 h / Ambient temperature

2: 1.) LDA / 1.) THF, -78 deg C, 10 min

3: H₂O₂ / tetrahydrofuran / 0.5 h / -15 °C

With dihydrogen peroxide; lithium diisopropyl amide; trichlorophosphate; In tetrahydrofuran;

upstream raw materials:

3,17β-bis(2-tetrahydropyranyloxy)estra-1,3,5(10)-triene

3-O-(tert-butyldimethylsilyl)-17β-O'-(tetrahydropyranyl)-19-oxoandrosta-2,4-diene-3,17β-diol

3,4-dihydro-2H-pyran

19-nortestosterone

Downstream raw materials:

estradiol