5-Dehydroepisterol

Base Information

• Chemical Name: 5-Dehydroepisterol
• CAS No.: 23582-83-4
• Molecular Formula: C₂₈H₄₄O
• Molecular Weight: 396.657
• UNII: W2W3AHW3TG
• DSSTox Substance ID: DTXSID90447480
• Nikkaji Number: J527.837F
• Wikipedia: 5-Dehydroepisterol
• Wikidata: Q4639583
• Metabolomics Workbench ID: 34798
• Mol file: 23582-83-4.mol

Synonyms:5-dehydroepisterol;23582-83-4;ergosta-5,7,24(28)-trien-3beta-ol;Campesta-7,24(28)-dien-3beta-ol;24-methylene-cholesta-5,7-dien-3beta-ol;(3S,9S,10R,13R,14R,17R)-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol;5-dehydro episterol;W2W3AHW3TG;SCHEMBL965835;CHEBI:52972;DTXSID90447480;LMST01030135;AKOS040732330;MS-26695;PD165254;HY-130703;CS-0111444;(3beta)-Ergosta-5,7,24(28)-trien-3-ol;Ergosta-5,7,24(28)-trien-3-ol, (3beta)-;Q4639583;(1R,3aR,7S,9aR,9bS,11aR)-9a,11a-Dimethyl-1-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,3a,6,7,8,9,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[a]phenanthren-7-ol

Chemical Property of 5-Dehydroepisterol

Chemical Property:

• Boiling Point: 503.2±39.0 °C(Predicted)
• PKA: 14.91±0.70(Predicted)
• Density: 1.00±0.1 g/cm3(Predicted)
• XLogP3: 8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 396.339216023
• Heavy Atom Count: 29
• Complexity: 712

Purity/Quality:

99% ^*data from raw suppliers

5-Dehydroepisterol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)C(=C)CCC(C)C1CCC2C1(CCC3C2=CC=C4C3(CCC(C4)O)C)C
• Isomeric SMILES: C[C@H](CCC(=C)C(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3C2=CC=C4[C@@]3(CC[C@@H](C4)O)C)C
• Uses: 5-Dehydroepisterol is a derivative of Episterol (E588710) a compound influencing Ergosterol biosynthesis, and thus acting as an antifungal agent.

Technology Process of 5-Dehydroepisterol

There total 14 articles about 5-Dehydroepisterol 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: 86.0%

tert-Butyl-[(3S,9S,10R,13R,14R,17R)-17-((R)-1,5-dimethyl-4-methylene-hexyl)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-dimethyl-silane (215022-91-6) → ergosta-5,7,24(28)-trien-3β-ol (23582-83-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1248/cpb.46.1454

Reference yield:

(3,3-dimethyloxiranyl)methanol (18511-56-3) → ergosta-5,7,24(28)-trien-3β-ol (23582-83-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 68 percent / n-BuLi / tetrahydrofuran; hexane / Ambient temperature

2: 86 percent / pyridine / 5 h / Ambient temperature

3: 77 percent / MeSO₂Cl, Et₃N / diethyl ether / a) 0 deg C, 5 h, b) RT, overnight

4: 75 percent / 20 percent KOH / ethanol / 1 h / Ambient temperature

5: 100 percent / H₂ / 5 percent Pd/C / methanol / 48 h / Ambient temperature

6: 75 percent / imidazole / dimethylformamide / 1 h / 55 °C

7: 1.) n-BuLi, 2.) 1,3-dimethyl-2-imidazolidinone / 1.) THF, hexane, -60 deg C, 30 min, 2.) THF, hexane, -20 deg C, 1 h

8: 5 percent Na/Hg, Na₂HPO₄ / tetrahydrofuran; methanol / Ambient temperature

9: pyridine / Ambient temperature

10: NaI / acetone / 3 h / Heating

11: 61 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / xylene / 0.5 h / Heating

12: 86 percent / n-Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

With pyridine; 1H-imidazole; 1,3-dimethyl-2-imidazolidinone; potassium hydroxide; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; N,N-dimethyl-formamide; acetone; xylene;

DOI:10.1248/cpb.46.1454

Reference yield:

3-methyl-2-buten-1-ol (556-82-1) → ergosta-5,7,24(28)-trien-3β-ol (23582-83-4)

Guidance literature:

Multi-step reaction with 13 steps

1: 65 percent / m-CPBA / CHCl₃ / Ambient temperature

2: 68 percent / n-BuLi / tetrahydrofuran; hexane / Ambient temperature

3: 86 percent / pyridine / 5 h / Ambient temperature

4: 77 percent / MeSO₂Cl, Et₃N / diethyl ether / a) 0 deg C, 5 h, b) RT, overnight

5: 75 percent / 20 percent KOH / ethanol / 1 h / Ambient temperature

6: 100 percent / H₂ / 5 percent Pd/C / methanol / 48 h / Ambient temperature

7: 75 percent / imidazole / dimethylformamide / 1 h / 55 °C

8: 1.) n-BuLi, 2.) 1,3-dimethyl-2-imidazolidinone / 1.) THF, hexane, -60 deg C, 30 min, 2.) THF, hexane, -20 deg C, 1 h

9: 5 percent Na/Hg, Na₂HPO₄ / tetrahydrofuran; methanol / Ambient temperature

10: pyridine / Ambient temperature

11: NaI / acetone / 3 h / Heating

12: 61 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / xylene / 0.5 h / Heating

13: 86 percent / n-Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

With pyridine; 1H-imidazole; 1,3-dimethyl-2-imidazolidinone; potassium hydroxide; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; chloroform; N,N-dimethyl-formamide; acetone; xylene;

DOI:10.1248/cpb.46.1454

upstream raw materials:

tert-Butyl-[(3S,9S,10R,13R,14R,17R)-17-((R)-1,5-dimethyl-4-methylene-hexyl)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-dimethyl-silane

(3,3-dimethyloxiranyl)methanol

3-methyl-2-<(phenylsulfonyl)methyl>-1-butanol

3-methyl-2-buten-1-ol

Refernces