(20R,23R,24S)-DINOSTERANE

Base Information

• Chemical Name: (20R,23R,24S)-DINOSTERANE
• CAS No.: 146276-33-7
• Molecular Formula: C₃₀H₅₄
• Molecular Weight: 414.759
• Mol file: 146276-33-7.mol

Synonyms:(20R,23R,24S)-DINOSTERANE;ALPHA, ALPHA, ALPHA (20R,23R,24S)-4A,23,24-TRIMETHYLCHOLESTANE

Chemical Property of (20R,23R,24S)-DINOSTERANE

Chemical Property:

• PSA: 0.00000
• LogP: 9.23580

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (20R,23R,24S)-DINOSTERANE

There total 27 articles about (20R,23R,24S)-DINOSTERANE 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: 96.0%

(20R,23R,24S)-5α-dinosteran-29-ol mesylate (148459-74-9) → (20R,23R,24S)-5α-Dinosterane (146276-33-7,133908-07-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 5h; Heating;

DOI:10.1021/jo00064a039

Reference yield:

Pregnenolone (145-13-1) → (20R,23R,24S)-5α-Dinosterane (146276-33-7,133908-07-3)

Guidance literature:

Multi-step reaction with 15 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

7: 82 percent / (n-Bu)3SnH, 2,2'-azobisisobutyronitrile / benzene / 4 h / Heating

8: 86 percent / 1 M aq. HCl, acetic acid / H₂O; tetrahydrofuran / 2 h / 25 °C

9: 91 percent / benzene / 1) reflux, 4.5 h, 2) 25 deg C, 12 h

10: 1) borane-THF, 2) 3 M NaOH, 30percent H₂O₂ / 1) THF, 25 deg C, 1 h, 2) water, 53 - 54 deg C, 3.5 h

11: 96 percent / NEt₃

12: 85 percent / NaI / acetone

14: 93 percent / NEt₃

15: 96 percent / LiAlH₄ / tetrahydrofuran / 5 h / Heating

With pyridine; 1-Methyl-4-piperidone; hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; borane-THF; 2,2'-azobis(isobutyronitrile); ammonia; dihydrogen peroxide; tri-n-butyl-tin hydride; aluminum isopropoxide; lithium; toluene-4-sulfonic acid; acetic acid; triethylamine; sodium iodide; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; toluene; benzene;

DOI:10.1021/jo00064a039

Reference yield:

(22E)-stigmasta-4,22-dien-3-one (20817-72-5,55722-32-2,83603-21-8) → (20R,23R,24S)-5α-Dinosterane (146276-33-7,133908-07-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 62 percent / NEt₃ / ethanol; H₂O / 72 h / Heating

2: 82 percent / lithium, liquid NH₃ / tetrahydrofuran / -78 °C

3: pyridine / CH₂Cl₂

4: tri-n-butyltin hydride, 2,2'-azobisisobutyronitrile / benzene / Heating

6: 96 percent / NEt₃

7: 85 percent / NaI / acetone

9: 93 percent / NEt₃

10: 96 percent / LiAlH₄ / tetrahydrofuran / 5 h / Heating

With pyridine; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); ammonia; tri-n-butyl-tin hydride; lithium; triethylamine; sodium iodide; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; benzene;

DOI:10.1021/jo00064a039

upstream raw materials:

(20R,23R,24S)-5α-dinosteran-29-ol mesylate

Pregnenolone

(22E)-stigmasta-4,22-dien-3-one

(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