4,4-Dimethyl-14alpha-hydroxymethyl-5alpha-cholest-8-en-3beta-ol

Base Information

• Chemical Name: 4,4-Dimethyl-14alpha-hydroxymethyl-5alpha-cholest-8-en-3beta-ol
• CAS No.: 59200-39-4
• Molecular Formula: C₃₀H₅₂O₂
• Molecular Weight: 444.742
• DSSTox Substance ID: DTXSID30974629
• Metabolomics Workbench ID: 34511
• Nikkaji Number: J426.577G
• Wikidata: Q27159341
• Mol file: 59200-39-4.mol

Synonyms:32-hydroxy-24,25-dihydrolanosterol;32-OH-24,25-dihydrolanosterol;lanost-8-en-3beta,32-diol

Chemical Property of 4,4-Dimethyl-14alpha-hydroxymethyl-5alpha-cholest-8-en-3beta-ol

Chemical Property:

• Vapor Pressure: 1.45E-13mmHg at 25°C
• Boiling Point: 532.6°C at 760 mmHg
• Flash Point: 213.6°C
• PSA: 40.46000
• Density: 1.01g/cm³
• LogP: 7.53140
• XLogP3: 8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 444.396730897
• Heavy Atom Count: 32
• Complexity: 735

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 4,4-Dimethyl-14alpha-hydroxymethyl-5alpha-cholest-8-en-3beta-ol

There total 5 articles about 4,4-Dimethyl-14alpha-hydroxymethyl-5alpha-cholest-8-en-3beta-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: 72.0%

(3S,5R,10S,13R,14S,17R)-14-Benzyloxymethyl-17-((R)-1,5-dimethyl-hexyl)-4,4,10,13-tetramethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol (136203-71-9) → lanost-8-en-3β,32-diol (59200-39-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1248/cpb.39.1647

Reference yield: 15.0%

3β-acetoxylanostan-7α,32-oxide (4489-03-6) → lanost-7-ene-3β,32-diol (5713-35-9) + lanost-8-en-3β,32-diol (59200-39-4) + lanost-6-ene-3β,32-diol (79884-30-3)

Guidance literature:

With pyridine hydrochloride; acetic anhydride;

DOI:10.1248/cpb.35.394

Reference yield:

2,2-Dimethyl-propionic acid (3S,5R,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-4,4,10,13-tetramethyl-15-oxo-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester (130257-83-9) → lanost-8-en-3β,32-diol (59200-39-4)

Guidance literature:

Multi-step reaction with 3 steps

2: Huang-Minlon reduction

3: 72 percent / H₂ / 5percent Pd-C / ethanol

With hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1248/cpb.39.1647

upstream raw materials:

(3S,5R,10S,13R,14S,17R)-14-Benzyloxymethyl-17-((R)-1,5-dimethyl-hexyl)-4,4,10,13-tetramethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

3β-acetoxylanostan-7α,32-oxide

3β-acetoxylanostan-7α-ol

2,2-Dimethyl-propionic acid (3S,5R,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-4,4,10,13-tetramethyl-15-oxo-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

Downstream raw materials:

3β-hydroxylanost-8-en-32-al