(-)-(1'R,4'R,6'R)-(Z)-5-(1',4'-dihydroxy-2',2',6'-trimethylcyclohexyl)-3-methyl-2-penten-4-yn-1-ol

Base Information

• Chemical Name: (-)-(1'R,4'R,6'R)-(Z)-5-(1',4'-dihydroxy-2',2',6'-trimethylcyclohexyl)-3-methyl-2-penten-4-yn-1-ol
• CAS No.: 160332-73-0
• Molecular Formula: C₁₅H₂₄O₃
• Molecular Weight: 252.354
• Mol file: 160332-73-0.mol

Synonyms:(-)-(1'R,4'R,6'R)-(Z)-5-(1',4'-dihydroxy-2',2',6'-trimethylcyclohexyl)-3-methyl-2-penten-4-yn-1-ol

Chemical Property of (-)-(1'R,4'R,6'R)-(Z)-5-(1',4'-dihydroxy-2',2',6'-trimethylcyclohexyl)-3-methyl-2-penten-4-yn-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1'R,4'R,6'R)-(Z)-5-(1',4'-dihydroxy-2',2',6'-trimethylcyclohexyl)-3-methyl-2-penten-4-yn-1-ol

There total 6 articles about (-)-(1'R,4'R,6'R)-(Z)-5-(1',4'-dihydroxy-2',2',6'-trimethylcyclohexyl)-3-methyl-2-penten-4-yn-1-ol 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%

(1S,4R,6R)-2,2,6-Trimethyl-1-[(Z)-3-methyl-5-(tetrahydro-pyran-2-yloxy)-pent-3-en-1-ynyl]-4-(tetrahydro-pyran-2-yloxy)-cyclohexanol → (-)-(1'R,4'R,6'R)-(Z)-5-(1',4'-dihydroxy-2',2',6'-trimethylcyclohexyl)-3-methyl-2-penten-4-yn-1-ol (160332-73-0)

Guidance literature:

With trifluoroacetic acid; In methanol; for 4h; Ambient temperature;

DOI:10.1016/0031-9422(95)00374-G

Reference yield: 68.0%

(4R,6R)-1-((Z)-5-Hydroxy-3-methyl-pent-3-en-1-ynyl)-2,2,6-trimethyl-4-trimethylsilanyloxy-cyclohexanol → (-)-(1'R,4'R,6'R)-(Z)-5-(1',4'-dihydroxy-2',2',6'-trimethylcyclohexyl)-3-methyl-2-penten-4-yn-1-ol (160332-73-0) + 2-Z-5-((1'R,4'R,6'R)-1',4'-dihydroxy-2',2',6'-trimethylcyclohexyl)-3-methyl-2-penten-4-yn-1-ol

Guidance literature:

With potassium hydroxide; In methanol; at 20 ℃; for 2h; Yields of byproduct given;

DOI:10.1016/0957-4166(94)80087-1

Reference yield:

(Z)-3-Methyl-2-penten-4-ynyl tetrahydropyranyl ether (41967-81-1) → (-)-(1'R,4'R,6'R)-(Z)-5-(1',4'-dihydroxy-2',2',6'-trimethylcyclohexyl)-3-methyl-2-penten-4-yn-1-ol (160332-73-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-BuLi / 1) THF, hexane, room temp. 30 min; 2) THF, hexane, room temp. 4 h

2: 85 percent / trifluoroacetic acid / methanol / 4 h / Ambient temperature

With n-butyllithium; trifluoroacetic acid; In methanol;

DOI:10.1016/0031-9422(95)00374-G

upstream raw materials:

(Z)-3-Methyl-2-penten-4-ynyl tetrahydropyranyl ether

(4R,6R)-2,2,6-Trimethyl-4-(tetrahydro-pyran-2-yloxy)-cyclohexanone

(4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexan-1-one

(4R,6R)-2,2,6-Trimethyl-4-trimethylsilanyloxy-cyclohexanone

Downstream raw materials:

(-)-(1'S,4'R,6'R)-(2Z,4E)-5-(1',4'-dihydroxy-2',2',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadien-1-ol

2-Z-5-((4'R)-4'-hydroxy-2',2',6'-trimethylcyclohex-1'-enyl)-3-methyl-2-penten-4-yn-1-al

(R)-4-<(E/Z)-5-hydroxy-3-methylpent-3-en-1-ynyl>-3,5,5-trimethylcyclohex-3-enol

9-Z-(3R,3'R)-diatoxanthin