(23R)-cholest-5-ene-3β,23-diol dibenzoate

Base Information

• Chemical Name: (23R)-cholest-5-ene-3β,23-diol dibenzoate
• CAS No.: 86794-55-0
• Molecular Formula: C₄₁H₅₄O₄
• Molecular Weight: 610.877
• Mol file: 86794-55-0.mol

Synonyms:

Chemical Property of (23R)-cholest-5-ene-3β,23-diol dibenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (23R)-cholest-5-ene-3β,23-diol dibenzoate

There total 15 articles about (23R)-cholest-5-ene-3β,23-diol dibenzoate 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:

3β-acetoxy-5-cholenic acid (19462-13-6) → (23R)-cholest-5-ene-3β,23-diol dibenzoate (86794-55-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 61 percent / cupric acetate, lead tetraacetate, pyridine / benzene / 3 h / Heating

2: 6.6 g / 5percent methanolic KOH / tetrahydrofuran / 16 h / Ambient temperature

3: 7.52 g / p-toluenesulfonic acid*H₂O / CH₂Cl₂ / 0.5 h / Ambient temperature

4: 1.) BH₃-THF complex, 2.) 3N sodium hydroxyde, 30percent H₂O₂ / 1.) THF, 0 deg C, 2.5 h, 2.) 0 deg C, 0.5 h

5: 2.06 g / pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 2 h

6: 1.) Mg / 1.) THF, 0 deg C, 100 min, 2.) 0 deg C, 1 h

7: 2.62 g / HCl / methanol; tetrahydrofuran / 2 h / Ambient temperature

8: pyridine / methanol; tetrahydrofuran / 0.5 h / 0 °C

9: 850 mg / 5percent methanolic KOH / tetrahydrofuran / 16 h / Ambient temperature

10: 64 mg / H₂ / platinum black / methanol / 0.5 h / Ambient temperature

11: 100 mg / pyridine

With pyridine; lead(IV) acetate; hydrogenchloride; potassium hydroxide; sodium hydroxide; borane-THF; hydrogen; dihydrogen peroxide; copper diacetate; sodium acetate; magnesium; pyridinium chlorochromate; toluene-4-sulfonic acid; platinum; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1248/cpb.31.394

Reference yield:

(3R)-3-((3S,10R,13R,17R)-10,13-dimethyl-3-((tetrahydro-2H-pyran-2-yl)oxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)butanal (51231-28-8) → (23R)-cholest-5-ene-3β,23-diol dibenzoate (86794-55-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) Mg / 1.) THF, 0 deg C, 100 min, 2.) 0 deg C, 1 h

2: 2.62 g / HCl / methanol; tetrahydrofuran / 2 h / Ambient temperature

3: pyridine / methanol; tetrahydrofuran / 0.5 h / 0 °C

4: 850 mg / 5percent methanolic KOH / tetrahydrofuran / 16 h / Ambient temperature

5: 64 mg / H₂ / platinum black / methanol / 0.5 h / Ambient temperature

6: 100 mg / pyridine

With pyridine; hydrogenchloride; potassium hydroxide; hydrogen; magnesium; platinum; In tetrahydrofuran; methanol;

DOI:10.1248/cpb.31.394

Reference yield:

3-[(tetrahydro-2H-pyran-2-yl)oxy]-24-norchol-5-en-23-ol (79190-31-1) → (23R)-cholest-5-ene-3β,23-diol dibenzoate (86794-55-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 2.06 g / pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 2 h

2: 1.) Mg / 1.) THF, 0 deg C, 100 min, 2.) 0 deg C, 1 h

3: 2.62 g / HCl / methanol; tetrahydrofuran / 2 h / Ambient temperature

4: pyridine / methanol; tetrahydrofuran / 0.5 h / 0 °C

5: 850 mg / 5percent methanolic KOH / tetrahydrofuran / 16 h / Ambient temperature

6: 64 mg / H₂ / platinum black / methanol / 0.5 h / Ambient temperature

7: 100 mg / pyridine

With pyridine; hydrogenchloride; potassium hydroxide; hydrogen; sodium acetate; magnesium; pyridinium chlorochromate; platinum; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1248/cpb.31.394

upstream raw materials:

benzoyl chloride

(Z)-6β-methoxy-3α,5-cyclo-5α-cholest-22-ene

(22E)-6β-methoxy-3α,5-cyclo-5α-cholest-22-ene

(3β,23R)-cholest-5-ene-3,23-diol