(R)-4-((1E,3E)-5-Hydroxy-3-methyl-penta-1,3-dienyl)-3,5,5-trimethyl-cyclohex-3-enol

Base Information

• Chemical Name: (R)-4-((1E,3E)-5-Hydroxy-3-methyl-penta-1,3-dienyl)-3,5,5-trimethyl-cyclohex-3-enol
• CAS No.: 956982-07-3
• Molecular Formula: C₁₅H₂₄O₂
• Molecular Weight: 236.354
• Mol file: 956982-07-3.mol

Synonyms:(R)-4-((1E,3E)-5-Hydroxy-3-methyl-penta-1,3-dienyl)-3,5,5-trimethyl-cyclohex-3-enol

Chemical Property of (R)-4-((1E,3E)-5-Hydroxy-3-methyl-penta-1,3-dienyl)-3,5,5-trimethyl-cyclohex-3-enol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-((1E,3E)-5-Hydroxy-3-methyl-penta-1,3-dienyl)-3,5,5-trimethyl-cyclohex-3-enol

There total 2 articles about (R)-4-((1E,3E)-5-Hydroxy-3-methyl-penta-1,3-dienyl)-3,5,5-trimethyl-cyclohex-3-enol 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: 85.0%

ethyl (2E,4E)-5-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexyl-1-enyl]-3-methylpenta-2,4-dienoate (395089-68-6) → (R)-4-((1E,3E)-5-Hydroxy-3-methyl-penta-1,3-dienyl)-3,5,5-trimethyl-cyclohex-3-enol (956982-07-3)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 0.25h;

DOI:10.1039/b710386g

Reference yield:

(R)-4-ethynyl-3,5,5-trimethylcyclohex-3-en-1-ol (118829-40-6,118829-45-1) → (R)-4-((1E,3E)-5-Hydroxy-3-methyl-penta-1,3-dienyl)-3,5,5-trimethyl-cyclohex-3-enol (956982-07-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Bu₃SnH; AIBN / 0.33 h / 130 °C

1.2: Pd₂dba3*CHCl₃; AsPh₃ / dimethylformamide / 50 °C

2.1: LiAlH₄

With lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride;

DOI:10.1248/cpb.49.1662

Reference yield:

(R)-4-((1E,3E)-5-Hydroxy-3-methyl-penta-1,3-dienyl)-3,5,5-trimethyl-cyclohex-3-enol (956982-07-3) → capsanthin (465-42-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 42 percent / NaOMe

With sodium methylate;

DOI:10.1248/cpb.49.1662

upstream raw materials:

ethyl (2E,4E)-5-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexyl-1-enyl]-3-methylpenta-2,4-dienoate

(R)-4-ethynyl-3,5,5-trimethylcyclohex-3-en-1-ol

Downstream raw materials:

(2E,4E)-5-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enyl]-3-methylpenta-2,4-dienal

capsanthin