4,4-Dimethyl-8,24-cholestadienol

Base Information

• Chemical Name: 4,4-Dimethyl-8,24-cholestadienol
• CAS No.: 7448-02-4
• Molecular Formula: C29H48 O
• Molecular Weight: 412.69
• DSSTox Substance ID: DTXSID60995988
• Mol file: 7448-02-4.mol

Synonyms:4,4-dimethyl-8,24-cholestadienol;4,4-dimethylcholesta-8,24-dien-3-ol;SCHEMBL6881894;DTXSID60995988;C05108

Chemical Property of 4,4-Dimethyl-8,24-cholestadienol

Chemical Property:

• Vapor Pressure: 7.07E-12mmHg at 25°C
• Boiling Point: 495.1°C at 760 mmHg
• Flash Point: 217.6°C
• PSA: 20.23000
• Density: 0.99g/cm³
• LogP: 8.08900
• Storage Temp.: -70°C
• XLogP3: 8.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 412.370516150
• Heavy Atom Count: 30
• Complexity: 723

Purity/Quality:

98%,99%, ^*data from raw suppliers

14-Norlanosterol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC=C(C)C)C1CCC2C1(CCC3=C2CCC4C3(CCC(C4(C)C)O)C)C
• Isomeric SMILES: C[C@H](CCC=C(C)C)[C@H]1CCC2[C@@]1(CCC3=C2CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)C
• Uses: 14-Norlanosterol, is a metabolite of Lanosterol (L174580). It is also a meiosis activating sterol (MAS), which is shown to have an important role in regulating meiosis and reproduction. 14-demethyl-lanosterol has been used to reduce cancer cell viability and increase cancer cell sensitivity to erlotinib.

Technology Process of 4,4-Dimethyl-8,24-cholestadienol

There total 21 articles about 4,4-Dimethyl-8,24-cholestadienol 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: 84.0%

4,4-Dimethylzymosterol benzoate (7408-47-1) → 4,4-dimethyl-5α-cholesta-8,24-dien-3β-ol (7448-02-4)

Guidance literature:

With diisobutylaluminium hydride; In hexane; dichloromethane; at 0 ℃; for 0.25h;

DOI:10.1021/ja00183a042

Reference yield:

3-methyl-butan-2-one (563-80-4) → 4,4-dimethyl-5α-cholesta-8,24-dien-3β-ol (7448-02-4)

Guidance literature:

Multi-step reaction with 15 steps

1: 1.) n-butyllithium, diisopropylamine / 1.) hexane, THF, -78 deg C, 15 min, 2.) THF, -78 deg C to 0 deg C, 1h

2: p-TSA, MgSO₄ / toluene; CHCl₃ / 3 h / 70 °C

3: H₂ / Lindlar / toluene; CHCl₃ / 12 h / 760 Torr

4: tert-butylamine-borane complex / CH₂Cl₂ / 1 h / Heating

5: 86 percent / pyridine, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 0.2 h / 0 °C

6: 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 1.) room temp., overnight, 2.) reflux, 30 min

7: 94 percent / tributylamine, 98percent formic acid / Pd(OAc)2(Ph₃P)2 / dimethylformamide / 0.5 h / 70 °C

8: K₂CO₃ / CH₂Cl₂; methanol / 0.08 h / 25 °C

9: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.03 h / 0 °C

10: borane-dimethyl sulfide complex / tetrahydrofuran / 2 h / Ambient temperature

11: pyridine, 4-(N,N-dimethylamino)pyridine / 12 h / 25 °C

12: Bu₃SnH, AIBN / toluene / 0.33 h / 90 °C

13: tetra-n-butylammonium fluoride / tetrahydrofuran / 12 h / Ambient temperature

14: 87 percent / Martin sulfurane / CH₂Cl₂ / 0.25 h / 0 °C

15: 84 percent / Dibal / CH₂Cl₂; hexane / 0.25 h / 0 °C

With pyridine; 2,6-dimethylpyridine; dmap; n-butyllithium; formic acid; 2,6-di-tert-butyl-4-methylpyridine; Martins sulfurane; tributyl-amine; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; diisobutylaluminium hydride; borane tert-butylamine; magnesium sulfate; potassium carbonate; toluene-4-sulfonic acid; diisopropylamine; Lindlar's catalyst; bis(triphenylphosphine) palladium (Il) acetate; In tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00183a042

Reference yield:

(3β,5α,20S)-3-(Benzoyloxy)-4,4-dimethyl-15-oxopregn-8,14-ene-20-carboxaldehyde (117438-93-4) → 4,4-dimethyl-5α-cholesta-8,24-dien-3β-ol (7448-02-4)

Guidance literature:

Multi-step reaction with 15 steps

1: 1.) n-butyllithium, diisopropylamine / 1.) hexane, THF, -78 deg C, 15 min, 2.) THF, -78 deg C to 0 deg C, 1h

2: p-TSA, MgSO₄ / toluene; CHCl₃ / 3 h / 70 °C

3: H₂ / Lindlar / toluene; CHCl₃ / 12 h / 760 Torr

4: tert-butylamine-borane complex / CH₂Cl₂ / 1 h / Heating

5: 86 percent / pyridine, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 0.2 h / 0 °C

6: 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 1.) room temp., overnight, 2.) reflux, 30 min

7: 94 percent / tributylamine, 98percent formic acid / Pd(OAc)2(Ph₃P)2 / dimethylformamide / 0.5 h / 70 °C

8: K₂CO₃ / CH₂Cl₂; methanol / 0.08 h / 25 °C

9: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.03 h / 0 °C

10: borane-dimethyl sulfide complex / tetrahydrofuran / 2 h / Ambient temperature

11: pyridine, 4-(N,N-dimethylamino)pyridine / 12 h / 25 °C

12: Bu₃SnH, AIBN / toluene / 0.33 h / 90 °C

13: tetra-n-butylammonium fluoride / tetrahydrofuran / 12 h / Ambient temperature

14: 87 percent / Martin sulfurane / CH₂Cl₂ / 0.25 h / 0 °C

15: 84 percent / Dibal / CH₂Cl₂; hexane / 0.25 h / 0 °C

With pyridine; 2,6-dimethylpyridine; dmap; n-butyllithium; formic acid; 2,6-di-tert-butyl-4-methylpyridine; Martins sulfurane; tributyl-amine; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; diisobutylaluminium hydride; borane tert-butylamine; magnesium sulfate; potassium carbonate; toluene-4-sulfonic acid; diisopropylamine; Lindlar's catalyst; bis(triphenylphosphine) palladium (Il) acetate; In tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00183a042

upstream raw materials:

tirucallol

mevalonolactone

4,4-Dimethylzymosterol benzoate

3-methyl-butan-2-one

Downstream raw materials:

[(3S,5R,10S,13R,14R,17R)-17-((R)-1,5-Dimethyl-hex-4-enyl)-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-yloxy]-trimethyl-silane

4,4-dimethyl-5α-cholesta-8-en-3β-ol

Refernces

• 1、 Hoshino, Tsutomu,Chiba, Akifumi,Abe, Naomi. "Lanosterol biosynthesis: The critical role of the methyl-29 group of 2,3-oxidosqualene for the correct folding of this substrate and for the construction of the five-membered D ring". supporting information. p. 13108 - 13116. Retrieved 2013/01/15.