(2S,3S,4R,6R)-2-[(E)-1,5-dimethylhex-1-enyl]-3-methoxy-4-p-methoxybenzyloxy-6-methylcyclohexanone

Base Information

• Chemical Name: (2S,3S,4R,6R)-2-[(E)-1,5-dimethylhex-1-enyl]-3-methoxy-4-p-methoxybenzyloxy-6-methylcyclohexanone
• CAS No.: 527755-55-1
• Molecular Formula: C₂₄H₃₆O₄
• Molecular Weight: 388.547
• Mol file: 527755-55-1.mol

Synonyms:(2S,3S,4R,6R)-2-[(E)-1,5-dimethylhex-1-enyl]-3-methoxy-4-p-methoxybenzyloxy-6-methylcyclohexanone

Chemical Property of (2S,3S,4R,6R)-2-[(E)-1,5-dimethylhex-1-enyl]-3-methoxy-4-p-methoxybenzyloxy-6-methylcyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R,6R)-2-[(E)-1,5-dimethylhex-1-enyl]-3-methoxy-4-p-methoxybenzyloxy-6-methylcyclohexanone

There total 2 articles about (2S,3S,4R,6R)-2-[(E)-1,5-dimethylhex-1-enyl]-3-methoxy-4-p-methoxybenzyloxy-6-methylcyclohexanone 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: 36.0%

(2S,3S,4R)-2-[(E)-1,5-dimethylhex-1-enyl]-3-methoxy-4-p-methoxybenzyloxy-6-methylenecyclohexanone (527755-53-9) → (2S,3S,4R,6R)-2-[(E)-1,5-dimethylhex-1-enyl]-3-methoxy-4-p-methoxybenzyloxy-6-methylcyclohexanone (527755-55-1) + (2S,3S,4R,6S)-2-[(E)-1,5-dimethylhex-1-enyl]-3-methoxy-4-p-methoxybenzyloxy-6-methylcyclohexanone

Guidance literature:

nickel; In tetrahydrofuran; water; at 0 ℃; for 2h;

DOI:10.1021/jo035065+

Reference yield:

1-[(1R,5S,6S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-5-((E)-1,5-dimethyl-hex-1-enyl)-6-methoxy-4-triethylsilanyloxy-cyclohex-3-enyloxymethyl]-4-methoxy-benzene → (2S,3S,4R,6R)-2-[(E)-1,5-dimethylhex-1-enyl]-3-methoxy-4-p-methoxybenzyloxy-6-methylcyclohexanone (527755-55-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 mg / trifluoroacetic acid / tetrahydrofuran; H₂O / 1.5 h / 20 °C

2: 16 percent / Raney nickel / tetrahydrofuran; H₂O / 2 h / 0 °C

With trifluoroacetic acid; nickel; In tetrahydrofuran; water;

DOI:10.1021/jo035065+

Reference yield: 54.0%

diiodomethane (75-11-6) + (2S,3S,4R,6R)-2-[(E)-1,5-dimethylhex-1-enyl]-3-methoxy-4-p-methoxybenzyloxy-6-methylcyclohexanone (527755-55-1) → (3R,4S,5S,6R,8R)-4-[(E)-1,5-dimethylhex-1-enyl]-5-methoxy-6-p-methoxybenzyloxy-8-methyl-1-oxaspiro[2.5]octane (527755-57-3)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 2.25h;

DOI:10.1021/jo035065+

upstream raw materials:

(2S,3S,4R)-2-[(E)-1,5-dimethylhex-1-enyl]-3-methoxy-4-p-methoxybenzyloxy-6-methylenecyclohexanone

Downstream raw materials:

(3R,4S,5S,6R,8R)-4-[(E)-1,5-dimethylhex-1-enyl]-5-methoxy-6-p-methoxybenzyloxy-8-methyl-1-oxaspiro[2.5]octane