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

Base Information

• Chemical Name: (2S,3S,4R)-3-methoxy-4-p-methoxybenzyloxy-2-[(E)-1,5-dimethylhex-1-enyl]cyclohexanone
• CAS No.: 527754-98-9
• Molecular Formula: C₂₃H₃₄O₄
• Molecular Weight: 374.521
• Mol file: 527754-98-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 16 articles about (2S,3S,4R)-3-methoxy-4-p-methoxybenzyloxy-2-[(E)-1,5-dimethylhex-1-enyl]cyclohexanone 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: 82.0%

(4R,5S,6S)-5-methoxy-4-p-methoxybenzyloxy-6-[(E)-1,5-dimethylhex-1-enyl]cyclohex-2-enone (527754-96-7) → (2S,3S,4R)-3-methoxy-4-p-methoxybenzyloxy-2-[(E)-1,5-dimethylhex-1-enyl]cyclohexanone (527754-98-9)

Guidance literature:

nickel; In tetrahydrofuran; water; at 0 ℃; for 0.333333h;

DOI:10.1021/jo035065+

Reference yield:

(E)-3,7-dimethyloct-3-enol (56134-54-4) → (2S,3S,4R)-3-methoxy-4-p-methoxybenzyloxy-2-[(E)-1,5-dimethylhex-1-enyl]cyclohexanone (527754-98-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 65 percent / CrO₃; H₂SO₄ / H₂O; acetone / 0.25 h / 0 °C

2.1: oxalyl chloride; DMF / CH₂Cl₂ / 4 h / 0 - 20 °C

3.1: 9.16 g / BuLi / tetrahydrofuran; hexane / -78 - 0 °C

4.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.5 h / -78 °C

4.2: 55 percent / tetrahydrofuran; hexane / 1 h / -78 °C

5.1: 5.83 g / tetrabutylammonium periodate / CHCl₃ / 2 h / 60 °C

6.1: trimethylaluminum / toluene; tetrahydrofuran / 0.5 h / 20 °C

6.2: 75 percent / toluene; tetrahydrofuran / 24 h / 20 °C

7.1: 93 percent / Ag₂O / diethyl ether / 8 h / 45 °C

8.1: 86 percent / tetrahydrofuran / 12 h / 20 °C

9.1: 78 percent / [(1,3-dimesitylimidazolidin-2-yl){P(c-hexyl)3}RuCl₂(=CHPh)] / toluene / 0.75 h / 70 °C

10.1: 82 percent / Raney nickel / H₂O; tetrahydrofuran / 0.33 h / 0 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; chromium(VI) oxide; n-butyllithium; oxalyl dichloride; sulfuric acid; trimethylaluminum; tetrabutylammonium periodite; N,N-dimethyl-formamide; silver(l) oxide; lithium diisopropyl amide; nickel; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; chloroform; water; acetone; toluene;

DOI:10.1021/jo035065+

Reference yield:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → (2S,3S,4R)-3-methoxy-4-p-methoxybenzyloxy-2-[(E)-1,5-dimethylhex-1-enyl]cyclohexanone (527754-98-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 70 percent / camphorsulfonic acid / CH₂Cl₂ / 24 h / 20 °C

2.1: DIBAL-H / toluene / 0.33 h / -78 °C

3.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.2: 55 percent / tetrahydrofuran; hexane / 1 h / -78 °C

4.1: 5.83 g / tetrabutylammonium periodate / CHCl₃ / 2 h / 60 °C

5.1: trimethylaluminum / toluene; tetrahydrofuran / 0.5 h / 20 °C

5.2: 75 percent / toluene; tetrahydrofuran / 24 h / 20 °C

6.1: 93 percent / Ag₂O / diethyl ether / 8 h / 45 °C

7.1: 86 percent / tetrahydrofuran / 12 h / 20 °C

8.1: 78 percent / [(1,3-dimesitylimidazolidin-2-yl){P(c-hexyl)3}RuCl₂(=CHPh)] / toluene / 0.75 h / 70 °C

9.1: 82 percent / Raney nickel / H₂O; tetrahydrofuran / 0.33 h / 0 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; camphor-10-sulfonic acid; trimethylaluminum; diisobutylaluminium hydride; tetrabutylammonium periodite; silver(l) oxide; lithium diisopropyl amide; nickel; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; chloroform; water; toluene;

DOI:10.1021/jo035065+

upstream raw materials:

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

(E)-3,7-dimethyloct-3-enol

O-(4-methoxybenzyl)-trichloroacetimidate

(E)-4-iodo-3-methylbut-3-en-1-ol

Downstream raw materials:

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

(3R,4S,5S,6R)-4-[(1S,2S)-1,2-epoxy-1,5-dimethylhexyl]-5-methoxy-6-p-methoxybenzyloxy-1-oxaspiro[2.5]octane

(3R,4S,5S,6R)-4-[(1R,2R)-1,2-epoxy-1,5-dimethylhexyl]-5-methoxy-6-p-methoxybenzyloxy-1-oxaspiro[2.5]octane