4α-methyl-3β-hydroxy-5α-pregnan-20-one ethylene ketal phenyl thiocarbonate

Base Information

• Chemical Name: 4α-methyl-3β-hydroxy-5α-pregnan-20-one ethylene ketal phenyl thiocarbonate
• CAS No.: 148552-73-2
• Molecular Formula: C₃₁H₄₄O₄S
• Molecular Weight: 512.754
• Mol file: 148552-73-2.mol

Synonyms:4α-methyl-3β-hydroxy-5α-pregnan-20-one ethylene ketal phenyl thiocarbonate

Chemical Property of 4α-methyl-3β-hydroxy-5α-pregnan-20-one ethylene ketal phenyl thiocarbonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4α-methyl-3β-hydroxy-5α-pregnan-20-one ethylene ketal phenyl thiocarbonate

There total 5 articles about 4α-methyl-3β-hydroxy-5α-pregnan-20-one ethylene ketal phenyl thiocarbonate 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: 78.0%

4α-methyl-3β-hydroxy-5α-pregnan-20-one ethylene ketal (148552-72-1) + phenylcarbonochloridothioate (1005-56-7) → 4α-methyl-3β-hydroxy-5α-pregnan-20-one ethylene ketal phenyl thiocarbonate (148552-73-2)

Guidance literature:

With pyridine; In dichloromethane;

DOI:10.1021/jo00064a039

Reference yield:

Pregnenolone (145-13-1) → 4α-methyl-3β-hydroxy-5α-pregnan-20-one ethylene ketal phenyl thiocarbonate (148552-73-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 79 percent / p-toluenesulfonic acid monohyrate

2: 78 percent / 1-methyl-4-piperidone, Al(O-i-Pr)3 / toluene / Heating

3: 54 percent / NEt₃ / ethanol; H₂O / 72 h / Heating

4: 54 percent / lithium, liquid NH₃ / tetrahydrofuran / 5 h / -78 °C

5: 87 percent / LiAlH₄ / tetrahydrofuran / 2.5 h / 25 °C

6: 78 percent / pyridine / CH₂Cl₂

With pyridine; 1-Methyl-4-piperidone; lithium aluminium tetrahydride; ammonia; aluminum isopropoxide; lithium; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; toluene;

DOI:10.1021/jo00064a039

Reference yield:

(3S,8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol (2415-36-3) → 4α-methyl-3β-hydroxy-5α-pregnan-20-one ethylene ketal phenyl thiocarbonate (148552-73-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 78 percent / 1-methyl-4-piperidone, Al(O-i-Pr)3 / toluene / Heating

2: 54 percent / NEt₃ / ethanol; H₂O / 72 h / Heating

3: 54 percent / lithium, liquid NH₃ / tetrahydrofuran / 5 h / -78 °C

4: 87 percent / LiAlH₄ / tetrahydrofuran / 2.5 h / 25 °C

5: 78 percent / pyridine / CH₂Cl₂

With pyridine; 1-Methyl-4-piperidone; lithium aluminium tetrahydride; ammonia; aluminum isopropoxide; lithium; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; toluene;

DOI:10.1021/jo00064a039

upstream raw materials:

4α-methyl-3β-hydroxy-5α-pregnan-20-one ethylene ketal

phenylcarbonochloridothioate

Pregnenolone

(3S,8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

Downstream raw materials:

(20R,23R,24S)-5α-Dinosterane

(20R,23R,24R)-5α-Dinosterane

(20R,23S,24S)-5α-Dinosterane

(20R,23S,24R)-5α-Dinosterane