20R23S24R-Dinosterane

Base Information

• Chemical Name: 20R23S24R-Dinosterane
• CAS No.: 146276-34-8
• Molecular Formula: C₃₀H₅₄
• Molecular Weight: 414.759
• DSSTox Substance ID: DTXSID501336950
• Nikkaji Number: J546.059J
• Mol file: 146276-34-8.mol

Synonyms:146276-34-8;(4R,5S,8S,9S,10S,13R,14S,17R)-4,10,13-Trimethyl-17-[(2R,4S,5R)-4,5,6-trimethylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene;20r 23s 24r-dinosterane;20R23S24R-DINOSTERANE;DTXSID501336950;(20R,23S,24R)-5alpha-Dinosterane;(4alpha,5alpha,23S)-4,23-Dimethylergostane

Chemical Property of 20R23S24R-Dinosterane

Chemical Property:

• Boiling Point: 469.7±12.0 °C(Predicted)
• PSA: 0.00000
• Density: 0.895±0.06 g/cm3(Predicted)
• LogP: 9.23580
• XLogP3: 11.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 5
• Exact Mass: 414.422551722
• Heavy Atom Count: 30
• Complexity: 591

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCCC2(C1CCC3C2CCC4(C3CCC4C(C)CC(C)C(C)C(C)C)C)C
• Isomeric SMILES: C[C@@H]1CCC[C@]2([C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4[C@H](C)C[C@H](C)[C@H](C)C(C)C)C)C

Technology Process of 20R23S24R-Dinosterane

There total 31 articles about 20R23S24R-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,23S,24R)-5α-dinosteran-29-ol mesylate (148552-86-7) → (20R,23S,24R)-5α-Dinosterane (146276-34-8,133908-07-3)

Guidance literature:

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

DOI:10.1021/jo00064a039

Reference yield:

Pregnenolone (145-13-1) → (20R,23S,24R)-5α-Dinosterane (146276-34-8,133908-07-3)

Guidance literature:

Multi-step reaction with 17 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: 96 percent / imidazole / dimethylformamide / 0.5 h / 60 °C

15: 1) H₂, 2) (n-Bu)4NF / 1) PtO₂ / 1) hexane, 25 deg C, 60 psi, 3 h, 2) THF, 25 deg C, 24 h

16: 93 percent / NEt₃

17: 96 percent / LiAlH₄ / tetrahydrofuran / 5 h / Heating

With pyridine; 1H-imidazole; 1-Methyl-4-piperidone; hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; borane-THF; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; ammonia; hydrogen; dihydrogen peroxide; tri-n-butyl-tin hydride; aluminum isopropoxide; lithium; toluene-4-sulfonic acid; acetic acid; triethylamine; sodium iodide; platinum(IV) oxide; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 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,23S,24R)-5α-Dinosterane (146276-34-8,133908-07-3)

Guidance literature:

Multi-step reaction with 12 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: 96 percent / imidazole / dimethylformamide / 0.5 h / 60 °C

10: 1) H₂, 2) (n-Bu)4NF / 1) PtO₂ / 1) hexane, 25 deg C, 60 psi, 3 h, 2) THF, 25 deg C, 24 h

11: 93 percent / NEt₃

12: 96 percent / LiAlH₄ / tetrahydrofuran / 5 h / Heating

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; ammonia; hydrogen; tri-n-butyl-tin hydride; lithium; triethylamine; sodium iodide; platinum(IV) oxide; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1021/jo00064a039

upstream raw materials:

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

3-methyl-butan-2-one

Pregnenolone

Methyl 3,4-dimethyl-2-pentenoate