4,4-Dimethylzymosterol benzoate

Base Information

• Chemical Name: 4,4-Dimethylzymosterol benzoate
• CAS No.: 7408-47-1
• Molecular Formula: C₃₆H₅₂O₂
• Molecular Weight: 516.808
• Mol file: 7408-47-1.mol

Synonyms:4,4-Dimethylzymosterol benzoate

Chemical Property of 4,4-Dimethylzymosterol benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,4-Dimethylzymosterol benzoate

There total 17 articles about 4,4-Dimethylzymosterol benzoate 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:

Benzoic acid (3S,5R,10S,13R,14R,17R)-17-((R)-4-hydroxy-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-yl ester (117439-18-6,117439-19-7) → 4,4-Dimethylzymosterol benzoate (7408-47-1) + Benzoic acid (3S,5S,10S,13R,14R,17R)-17-((E)-(R)-1,5-dimethyl-hex-3-enyl)-10,13-dimethyl-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester (117168-35-1)

Guidance literature:

With Martins sulfurane; In dichloromethane; at 0 ℃; for 0.25h;

DOI:10.1021/ja00183a042

Reference yield:

3-methyl-butan-2-one (563-80-4) → 4,4-Dimethylzymosterol benzoate (7408-47-1)

Guidance literature:

Multi-step reaction with 14 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

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; borane tert-butylamine; magnesium sulfate; potassium carbonate; toluene-4-sulfonic acid; diisopropylamine; Lindlar's catalyst; bis(triphenylphosphine) palladium (Il) acetate; In tetrahydrofuran; methanol; 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-Dimethylzymosterol benzoate (7408-47-1)

Guidance literature:

Multi-step reaction with 14 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

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; borane tert-butylamine; magnesium sulfate; potassium carbonate; toluene-4-sulfonic acid; diisopropylamine; Lindlar's catalyst; bis(triphenylphosphine) palladium (Il) acetate; In tetrahydrofuran; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00183a042

upstream raw materials:

Benzoic acid (3S,5R,10S,13R,14R,17R)-17-((R)-4-hydroxy-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-yl ester

3-methyl-butan-2-one

(3β,5α,20S)-3-(Benzoyloxy)-4,4-dimethyl-15-oxopregn-8,14-ene-20-carboxaldehyde

3β-(Benzoyloxy)-24-hydroxy-4,4-dimethyl-5α-cholest-8(14)-ene-15-one

Downstream raw materials:

4,4-dimethyl-5α-cholesta-8,24-dien-3β-ol

Refernces