[(3R,5R,8R,9S,10S,13R,14S,17R)-17-[(2R)-5,5-diphenylpent-4-en-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate

Base Information

• Chemical Name: [(3R,5R,8R,9S,10S,13R,14S,17R)-17-[(2R)-5,5-diphenylpent-4-en-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS No.: 4144-29-0
• Molecular Formula: C38H50 O2
• Molecular Weight: 538.814
• European Community (EC) Number: 685-924-8
• NSC Number: 8111
• DSSTox Substance ID: DTXSID60961683
• Mol file: 4144-29-0.mol

Synonyms:4144-29-0;NSC8111;24,24-diphenylchol-23-en-3-yl acetate;DTXSID60961683;NSC-8111

Chemical Property of [(3R,5R,8R,9S,10S,13R,14S,17R)-17-[(2R)-5,5-diphenylpent-4-en-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate

Chemical Property:

• Vapor Pressure: 7.45E-15mmHg at 25°C
• Boiling Point: 610.7°Cat760mmHg
• Flash Point: 322.3°C
• Density: 1.08g/cm³
• XLogP3: 11.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 538.381080833
• Heavy Atom Count: 40
• Complexity: 889

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC=C(C1=CC=CC=C1)C2=CC=CC=C2)C3CCC4C3(CCC5C4CCC6C5(CCC(C6)OC(=O)C)C)C
• Isomeric SMILES: C[C@H](CC=C(C1=CC=CC=C1)C2=CC=CC=C2)[C@H]3CC[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC[C@H]6[C@@]5(CC[C@H](C6)OC(=O)C)C)C

Technology Process of [(3R,5R,8R,9S,10S,13R,14S,17R)-17-[(2R)-5,5-diphenylpent-4-en-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate

There total 13 articles about [(3R,5R,8R,9S,10S,13R,14S,17R)-17-[(2R)-5,5-diphenylpent-4-en-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] 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:

→ acetic acid-(24.24-diphenyl-5β-cholen-(23)-yl-(3α)-ester) (4144-29-0)

Guidance literature:

DOI:10.1021/ja01860a036

Reference yield:

methyl lithocholate (1249-75-8,5405-42-5,15074-01-8,15074-02-9,20231-51-0,63814-53-9,106757-10-2,125412-30-8) + phenylmagnesium bromide → 3α-acetoxy-24,24-diphenyl-5β-chol-23-ene (4144-29-0)

Guidance literature:

With benzene; anschliessend mit Acetanhydrid in Pyridin erwaermen und Erhitzen des Reaktionsprodukts in Essigsaeure;

DOI:10.1021/jo01094a602

Reference yield:

methyl 5-cholenoate (20231-57-6) → acetic acid-(24.24-diphenyl-5α-cholen-(23)-yl-(3β)-ester) (4144-29-0)

Guidance literature:

Multi-step reaction with 4 steps

1: platinum; acetic acid; ethanol / Hydrogenation

2: diethyl ether; benzene / Kochen der vom Aether befreiten Reaktionsloesung

3: iodine; benzene

4: pyridine / Erwaermen auf dem Dampfbad

With pyridine; diethyl ether; ethanol; iodine; acetic acid; platinum; benzene;

DOI:10.1002/hlca.19460290107

upstream raw materials:

methyl lithocholate

3β-hydroxy-10.13-dimethyl-17β-((R)-1-methyl-4.4-diphenyl-buten-(3)-yl)-5α-gonane

acetic anhydride

acetic acid

Downstream raw materials:

dihydroprogesterone

isopregnanolone

5α-pregnan-3β,20α-diol

acetic acid-(23ξ-bromo-24-hydroxy-24,24-diphenyl-5α-cholanyl-(3β)-ester)