Egiceradienol

Base Information

• Chemical Name: Egiceradienol
• CAS No.: 6040-30-8
• Molecular Formula: C₂₉H₄₆O
• Molecular Weight: 410.684
• DSSTox Substance ID: DTXSID601298575
• Nikkaji Number: J38.505K
• Wikidata: Q105276137
• Mol file: 6040-30-8.mol

Synonyms:6040-30-8;Egiceradienol;DTXSID601298575;(3beta)-28-Noroleana-12,17-dien-3-ol

Chemical Property of Egiceradienol

Chemical Property:

• PSA: 20.23000
• LogP: 7.84300
• XLogP3: 7.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 410.354866087
• Heavy Atom Count: 30
• Complexity: 812

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC2=C(C1)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)C
• Isomeric SMILES: C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CCC5=C4CC(CC5)(C)C)C)C)(C)C)O

Technology Process of Egiceradienol

There total 20 articles about Egiceradienol 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: 92.0%

tert-Butyl-((3S,4aR,6aR,6bS,14aR,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,9,10,11,12,14,14a,14b-octadecahydro-picen-3-yloxy)-dimethyl-silane (251980-62-8) → aegiceradienol (6040-30-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In N,N-dimethyl-formamide; at 50 ℃; for 14h;

DOI:10.1021/ja992411p

Reference yield:

3β-benzoyloxy-28-nor-oleana-12,17-diene (107387-66-6) → aegiceradienol (6040-30-8)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane;

DOI:10.1021/ja00072a064

Reference yield:

3,3-dimethylcyclohexanone (2979-19-3) → aegiceradienol (6040-30-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: PBr₃ / CHCl₃ / 0.5 h / 70 °C

1.2: CHCl₃ / 1.5 h / 70 °C

2.1: DIBAL / diethyl ether; toluene / 1 h / 23 °C

3.1: Et₃N / tetrahydrofuran / 0.5 h / -40 °C

4.1: 92 percent / LiBr / tetrahydrofuran / 1 h / 0 °C

5.1: 84 percent

6.1: MeAlCl₂ / hexane; CH₂Cl₂ / 0.5 h / -78 °C

7.1: imidazole / CH₂Cl₂ / 20 h / Heating

8.1: LDA / tetrahydrofuran / 1.5 h / -78 - 0 °C

8.2: 84 percent / tetrahydrofuran / 2 h / -78 - 23 °C

9.1: Pd(PPh₃)4; LiCl; Me₃SnSnMe₃ / tetrahydrofuran / 16 h / Heating

9.2: 60 percent / CuCl / dimethylformamide / 0.33 h / 60 °C

10.1: 92 percent / TBAF / dimethylformamide / 14 h / 50 °C

With 1H-imidazole; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; hexamethyldistannane; methylaluminum dichloride; phosphorus tribromide; diisobutylaluminium hydride; triethylamine; lithium chloride; lithium bromide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; 1.1: phosphorylation / 1.2: Formylation / 2.1: Reduction / 3.1: mesylation / 4.1: Bromination / 6.1: Cyclization / 7.1: silylation / 8.1: deprotonation / 8.2: triflation / 9.1: trimethylstannylation / 9.2: Cyclization / 10.1: desilylation;

DOI:10.1021/ja992411p

upstream raw materials:

Morolic acid

echinocystic acid

aegiceradienyl acetate

3β-benzoyloxy-28-nor-oleana-12,17-diene

Downstream raw materials:

3β-benzoyloxy-28-nor-oleana-12,17-diene

Refernces

• 1、 Huang, Alan X.,Xiong, Zhaoming,Corey. "An exceptionally short and simple enantioselective total synthesis of pentacyclic triterpenes of the β-amyrin family". . p. 9999 - 10003. Retrieved 2007/10/03.
• 2、 Sundararamaiah, T.,Rao, V. Vishwanath. "Oxidative Decarboxylation: Partial Synthesis of Aegiceradienol (nor Echinocystadienol)". . p. 74 - 76. Retrieved 2007/10/02.