1-[(3S,5R,10S,13R,14R,17S)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone

Base Information

• Chemical Name: 1-[(3S,5R,10S,13R,14R,17S)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
• CAS No.: 5217-14-1
• Molecular Formula: C24H38O2
• Molecular Weight: 358.5573
• NSC Number: 81401
• Nikkaji Number: J1.353.862J
• Mol file: 5217-14-1.mol

Synonyms:NSC81401;NSC-81401;5217-14-1

Chemical Property of 1-[(3S,5R,10S,13R,14R,17S)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone

Chemical Property:

• Vapor Pressure: 3.35E-10mmHg at 25°C
• Boiling Point: 455.3°C at 760 mmHg
• Flash Point: 193.9°C
• Density: 1.06g/cm³
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 358.287180451
• Heavy Atom Count: 26
• Complexity: 674

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1CCC2(C1(CCC3=C2CCC4C3(CCC(C4(C)C)O)C)C)C
• Isomeric SMILES: CC(=O)[C@H]1CC[C@@]2([C@@]1(CCC3=C2CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)C)C

Technology Process of 1-[(3S,5R,10S,13R,14R,17S)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone

There total 13 articles about 1-[(3S,5R,10S,13R,14R,17S)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone 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:

3β-Acetoxy-4,4,14α-trimethyl-Δ8-5α-pregnen-on-(20) (27868-09-3) → 3β-Hydroxy-4,4,14-trimethyl-Δ8-trimethyl-5α-pregnen-20-on (5217-14-1)

Guidance literature:

With potassium hydroxide; In methanol; benzene;

Reference yield:

3β-acetoxy-25,26,27-trinorlanost-8-ene-24-carboxylic acid (30655-15-3) → 3β-Hydroxy-4,4,14-trimethyl-Δ8-trimethyl-5α-pregnen-20-on (5217-14-1)

Guidance literature:

Multi-step reaction with 4 steps

1: Pb(OAc)4, Cu(OAc)2, Py / benzene

2: (i) Li, H₂NCH₂CH₂NH₂, (ii) /BRN= 385737/, Py

3: (i) O₃, CH₂Cl₂, MeOH, (ii) Me₂S

4: KOH / methanol; benzene

With pyridine; lead(IV) acetate; potassium hydroxide; copper diacetate; In methanol; benzene;

Reference yield:

(20S)-3β-acetoxy-23,24,25,26,27-pentanorlanost-8-en-22-al (27868-10-6) → 3β-Hydroxy-4,4,14-trimethyl-Δ8-trimethyl-5α-pregnen-20-on (5217-14-1)

Guidance literature:

Multi-step reaction with 2 steps

1: (i) pyrrolidine, benzene, (ii) OsO₄, dioxane

2: KOH / methanol

With potassium hydroxide; In methanol;

DOI:10.1002/jlac.19707420121

upstream raw materials:

3β-Acetoxy-4,4,14α-trimethyl-Δ⁸-5α-pregnen-on-(20)

3β-acetoxy-25,26,27-trinorlanost-8-ene-24-carboxylic acid

(20S)-3β-acetoxy-23,24,25,26,27-pentanorlanost-8-en-22-al

3β-acetoxy-24,25,26,27-tetranorlanosta-8,22-diene

Downstream raw materials:

d-4,4,14-trimethyl-5α,14α-pregn-8-ene-3,20-dione

Refernces

• 1、 Habermehl,Volkwein. "3-beta-hydroxy-4,4,14-trimethyl-delta-8-5-alpha-pregnen-20-one". . p. 145 - 151. Retrieved 2007/10/13.