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

Base Information

• Chemical Name: (3R,4S,5S,6R)-4-[(E)-1,5-dimethylhex-1-enyl]-5-methoxy-6-p-methoxybenzyloxy-1-oxaspiro[2.5]octane
• CAS No.: 527754-99-0
• Molecular Formula: C₂₄H₃₆O₄
• Molecular Weight: 388.547
• Mol file: 527754-99-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 17 articles about (3R,4S,5S,6R)-4-[(E)-1,5-dimethylhex-1-enyl]-5-methoxy-6-p-methoxybenzyloxy-1-oxaspiro[2.5]octane 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: 77.0%

trimethylsulfoxonium iodide (1774-47-6) + (2S,3S,4R)-3-methoxy-4-p-methoxybenzyloxy-2-[(E)-1,5-dimethylhex-1-enyl]cyclohexanone (527754-98-9) → (3R,4S,5S,6R)-4-[(E)-1,5-dimethylhex-1-enyl]-5-methoxy-6-p-methoxybenzyloxy-1-oxaspiro[2.5]octane (527754-99-0)

Guidance literature:

trimethylsulfoxonium iodide; With sodium hydride; In dimethyl sulfoxide; at 20 ℃; for 1h;

With lithium iodide; In tetrahydrofuran; dimethyl sulfoxide; for 0.666667h;

(2S,3S,4R)-3-methoxy-4-p-methoxybenzyloxy-2-[(E)-1,5-dimethylhex-1-enyl]cyclohexanone; In tetrahydrofuran; dimethyl sulfoxide; at 20 ℃; for 0.5h;

DOI:10.1021/jo035065+

Reference yield:

(E)-3,7-dimethyloct-3-enol (56134-54-4) → (3R,4S,5S,6R)-4-[(E)-1,5-dimethylhex-1-enyl]-5-methoxy-6-p-methoxybenzyloxy-1-oxaspiro[2.5]octane (527754-99-0)

Guidance literature:

Multi-step reaction with 11 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

11.1: NaH / dimethylsulfoxide / 1 h / 20 °C

11.2: lithium iodide / dimethylsulfoxide; tetrahydrofuran / 0.67 h

11.3: 77 percent / dimethylsulfoxide; tetrahydrofuran / 0.5 h / 20 °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; sodium hydride; tetrabutylammonium periodite; N,N-dimethyl-formamide; silver(l) oxide; lithium diisopropyl amide; nickel; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; chloroform; water; dimethyl sulfoxide; acetone; toluene;

DOI:10.1021/jo035065+

Reference yield:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → (3R,4S,5S,6R)-4-[(E)-1,5-dimethylhex-1-enyl]-5-methoxy-6-p-methoxybenzyloxy-1-oxaspiro[2.5]octane (527754-99-0)

Guidance literature:

Multi-step reaction with 10 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

10.1: NaH / dimethylsulfoxide / 1 h / 20 °C

10.2: lithium iodide / dimethylsulfoxide; tetrahydrofuran / 0.67 h

10.3: 77 percent / dimethylsulfoxide; tetrahydrofuran / 0.5 h / 20 °C

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

DOI:10.1021/jo035065+

upstream raw materials:

trimethylsulfoxonium iodide

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

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

O-(4-methoxybenzyl)-trichloroacetimidate

Downstream raw materials:

(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