Petrosterol

Base Information

• Chemical Name: Petrosterol
• CAS No.: 67314-15-2
• Molecular Formula: C29H48O
• Molecular Weight: 412.7
• Mol file: 67314-15-2.mol

Synonyms:EINECS 265-376-2;

Chemical Property of Petrosterol

Chemical Property:

• Vapor Pressure: 2.34E-12mmHg at 25°C
• Boiling Point: 506°Cat760mmHg
• Flash Point: 219.7°C
• PSA: 17.07000
• Density: 1.01g/cm³
• LogP: 4.81370

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Petrosterol

There total 32 articles about Petrosterol 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: 55.0%

(20R/S,24R,25R,26R)-24,26-Dimethyl-6β-methoxy-3α,5;25,27-dicyclo-5α-cholestane → (24R,25R,26R)-petrosterol (67314-15-2) + (3S,8S,9S,10R,13R,14S,17R)-10,13-Dimethyl-17-[(1S,4R)-1-methyl-4-((1R,2R)-2-methyl-cyclopropyl)-pentyl]-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

Guidance literature:

With toluene-4-sulfonic acid; In 1,4-dioxane; at 80 ℃; for 1h;

DOI:10.1039/p19960002291

Reference yield:

trans-2-methylcyclopropanecarboxylic acid chloride (42274-66-8,52194-64-6,52194-65-7,60733-34-8) → (24R,25R,26R)-petrosterol (67314-15-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 2.9 g / 2.4 M n-butyllithium / tetrahydrofuran / 0 °C

2: 77 percent / benzene / 10 h / Heating

3: 80 percent / 0.55 M NaBH₄ / pyridine / 4 h

4: 94 percent / 2.4 M n-butyllithium / tetrahydrofuran / 4 h / 0 °C

5: 1.) 1 M borane; 2.) 30 percent H₂O₂, dild. NaOH / 1.) THF, 0 deg C, 2h

6: pyridine / 24 h

7: 1.) LiAlH₄; 2.) p-toluenesulfonic acid / 1.) Et₂O, 12 h; 2.) dioxane/water, reflux, 1 h

With sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; borane; dihydrogen peroxide; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; benzene;

DOI:10.1021/ja00331a035

Reference yield:

triphenylphopshoranilidenemethyl (2'-methyl)cyclopropyl ketone (91228-92-1) → (24R,25R,26R)-petrosterol (67314-15-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 77 percent / benzene / 10 h / Heating

2: 80 percent / 0.55 M NaBH₄ / pyridine / 4 h

3: 94 percent / 2.4 M n-butyllithium / tetrahydrofuran / 4 h / 0 °C

4: 1.) 1 M borane; 2.) 30 percent H₂O₂, dild. NaOH / 1.) THF, 0 deg C, 2h

5: pyridine / 24 h

6: 1.) LiAlH₄; 2.) p-toluenesulfonic acid / 1.) Et₂O, 12 h; 2.) dioxane/water, reflux, 1 h

With sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; borane; dihydrogen peroxide; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; benzene;

DOI:10.1021/ja00331a035

upstream raw materials:

Toluene-4-sulfonic acid (2R,5R)-5-((1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-2-((1R,2R)-2-methyl-cyclopropyl)-hexyl ester

methyl (3S,4R)-4-(tert-butyldimethylsiloxy)-3,7-dimethyl-6-octenoate

(1R,2R,3R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(1-chloro-1-methyl-ethyl)-2-methyl-cyclopentanecarboxylic acid methyl ester

(1R,2R)-2-<(1R)-3-Hydroxy-1-methylpropyl>-1-methylcyclopropane

Downstream raw materials:

5α,6α-epoxy-petrosterol

(24R,25R)-24-methyl-26-methylenecholest-5-en-3β-ol

(E)-24-methyl-26,26-dimethyl-27-norcholesta-5,23-dien-3β-ol

(Z)-24-methyl-26,26-dimethyl-27-norcholesta-5,23-dien-3β-ol

Refernces

• 1、 Fujimoto, Yoshinori,Ohhana, Mitsunori,Terasawa, Takeshi,Ikekawa, Nobuo. "Stereocontrolled Synthesis of Petrosterol". . p. 3239 - 3242. Retrieved 2007/10/02.