Cholest-5-ene-3,7,22-triol

Base Information

• Chemical Name: Cholest-5-ene-3,7,22-triol
• CAS No.: 104786-66-5
• Molecular Formula: C₂₇H₄₆O₃
• Molecular Weight: 418.66
• DSSTox Substance ID: DTXSID10909212
• Wikidata: Q27158932
• Mol file: 104786-66-5.mol

Synonyms:cholest-5-ene-3,7,22-triol;cholest-5-ene-3,7,22-triol, (3beta,7beta,22R)-isomer

Chemical Property of Cholest-5-ene-3,7,22-triol

Chemical Property:

• Vapor Pressure: 2.58E-14mmHg at 25°C
• Boiling Point: 548.5°Cat760mmHg
• Flash Point: 230.5°C
• PSA: 60.69000
• Density: 1.08g/cm³
• LogP: 5.33030
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 418.34469533
• Heavy Atom Count: 30
• Complexity: 657

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCC(C(C)C1CCC2C1(CCC3C2C(C=C4C3(CCC(C4)O)C)O)C)O
• Isomeric SMILES: C[C@@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H](C=C4[C@@]3(CC[C@@H](C4)O)C)O)C)[C@@H](CCC(C)C)O

Technology Process of Cholest-5-ene-3,7,22-triol

There total 7 articles about Cholest-5-ene-3,7,22-triol 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:

(Methyl-3-but-2-enyl)triphenylarsonium bromide (27127-35-1) → (22R)-7α,22-Dihydroxycholesterol (104786-66-5)

Guidance literature:

Multi-step reaction with 6 steps

1: NaBF₄ / H₂O

3: 97 percent / H₂ / 5percent Pd-C / ethyl acetate / 1.33 h / Ambient temperature

4: 1.) MsCl, pyridine, 2.) 18-crown-6, KO₂ / 1.) 0 deg C, 0.5 h; room temp., 4.5 h, 2.) DMSO, DMF, room temp., 2 h

5: 1.) Ac₂O, 2.) Na₂Cr₂O₇ / 1.) reflux, 1.75 h, 2.) 55 deg C, 16 h

6: 1.) L-Selectride, 2.) LiAlH₄ / 1.) THF, -78 deg C, 15 min, 2.) room temp., 15 min

With pyridine; lithium aluminium tetrahydride; sodium tetrafluoroborate; sodium dichromate; 18-crown-6 ether; hydrogen; acetic anhydride; L-Selectride; methanesulfonyl chloride; palladium on activated charcoal; In water; ethyl acetate;

DOI:10.1055/s-1987-28147

Reference yield:

(22S)-22-Hydroxy-6β-methoxy-3α,5-cyclo-5α-cholest-24-ene (54604-95-4,54649-48-8) → (22R)-7α,22-Dihydroxycholesterol (104786-66-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / H₂ / 5percent Pd-C / ethyl acetate / 1.33 h / Ambient temperature

2: 1.) MsCl, pyridine, 2.) 18-crown-6, KO₂ / 1.) 0 deg C, 0.5 h; room temp., 4.5 h, 2.) DMSO, DMF, room temp., 2 h

3: 1.) Ac₂O, 2.) Na₂Cr₂O₇ / 1.) reflux, 1.75 h, 2.) 55 deg C, 16 h

4: 1.) L-Selectride, 2.) LiAlH₄ / 1.) THF, -78 deg C, 15 min, 2.) room temp., 15 min

With pyridine; lithium aluminium tetrahydride; sodium dichromate; 18-crown-6 ether; hydrogen; acetic anhydride; L-Selectride; methanesulfonyl chloride; palladium on activated charcoal; In ethyl acetate;

DOI:10.1055/s-1987-28147

Reference yield:

(Methyl-3-but-2-enyl)triphenylarsonium tetrafluoroborate → (22R)-7α,22-Dihydroxycholesterol (104786-66-5)

Guidance literature:

Multi-step reaction with 5 steps

2: 97 percent / H₂ / 5percent Pd-C / ethyl acetate / 1.33 h / Ambient temperature

3: 1.) MsCl, pyridine, 2.) 18-crown-6, KO₂ / 1.) 0 deg C, 0.5 h; room temp., 4.5 h, 2.) DMSO, DMF, room temp., 2 h

4: 1.) Ac₂O, 2.) Na₂Cr₂O₇ / 1.) reflux, 1.75 h, 2.) 55 deg C, 16 h

5: 1.) L-Selectride, 2.) LiAlH₄ / 1.) THF, -78 deg C, 15 min, 2.) room temp., 15 min

With pyridine; lithium aluminium tetrahydride; sodium dichromate; 18-crown-6 ether; hydrogen; acetic anhydride; L-Selectride; methanesulfonyl chloride; palladium on activated charcoal; In ethyl acetate;

DOI:10.1055/s-1987-28147

upstream raw materials:

(22R)-22-Hydroxy-7-oxocholesterol diacetate

(Methyl-3-but-2-enyl)triphenylarsonium bromide

(22S)-22-Hydroxy-6β-methoxy-3α,5-cyclo-5α-cholest-24-ene

(22R)-22-Hydroxy-6β-methoxy-3α,5-cyclo-5α-cholestane

Refernces