6-[(2R,3E)-5-(benzyloxy)pent-3-en-2-yl]-2-[(2E)-4-hydroxy-4-methylpent-2-enyl]-4-(methoxymethoxy)-3-methylphenol

Base Information

• Chemical Name: 6-[(2R,3E)-5-(benzyloxy)pent-3-en-2-yl]-2-[(2E)-4-hydroxy-4-methylpent-2-enyl]-4-(methoxymethoxy)-3-methylphenol
• CAS No.: 1528746-76-0
• Molecular Formula: C₂₇H₃₆O₅
• Molecular Weight: 440.58

Synonyms:6-[(2R,3E)-5-(benzyloxy)pent-3-en-2-yl]-2-[(2E)-4-hydroxy-4-methylpent-2-enyl]-4-(methoxymethoxy)-3-methylphenol

Chemical Property of 6-[(2R,3E)-5-(benzyloxy)pent-3-en-2-yl]-2-[(2E)-4-hydroxy-4-methylpent-2-enyl]-4-(methoxymethoxy)-3-methylphenol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of 6-[(2R,3E)-5-(benzyloxy)pent-3-en-2-yl]-2-[(2E)-4-hydroxy-4-methylpent-2-enyl]-4-(methoxymethoxy)-3-methylphenol

There total 7 articles about 6-[(2R,3E)-5-(benzyloxy)pent-3-en-2-yl]-2-[(2E)-4-hydroxy-4-methylpent-2-enyl]-4-(methoxymethoxy)-3-methylphenol 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: 26.0%

(3R)-3-{2-[(2R,3E)-5-(benzyloxy)pent-3-en-2-yl]-4-(methoxymethoxy)-5-methylphenoxy}-2-methylpent-4-en-2-ol (1528746-75-9) → 6-[(2R,3E)-5-(benzyloxy)pent-3-en-2-yl]-2-[(2E)-4-hydroxy-4-methylpent-2-enyl]-4-(methoxymethoxy)-3-methylphenol (1528746-76-0)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In toluene; at 110 ℃; for 53h; Inert atmosphere;

DOI:10.1016/j.tet.2013.11.070

Reference yield:

(2R,3E)-2-[5-(benzyloxy)pent-3-en-2-yl]-4-(methoxymethoxy)-5-methylphenol (1313708-38-1) → 6-[(2R,3E)-5-(benzyloxy)pent-3-en-2-yl]-2-[(2E)-4-hydroxy-4-methylpent-2-enyl]-4-(methoxymethoxy)-3-methylphenol (1528746-76-0)

Guidance literature:

Multi-step reaction with 6 steps

1: potassium carbonate / acetonitrile / 4 h / 20 °C / Inert atmosphere

2: tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

4: tributylphosphine / tetrahydrofuran / 0.5 h / 20 °C

5: dihydrogen peroxide / tetrahydrofuran; water / 0.25 h / 60 °C

6: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 53 h / 110 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tributylphosphine; tetrabutyl ammonium fluoride; dihydrogen peroxide; potassium carbonate; In tetrahydrofuran; water; toluene; acetonitrile;

DOI:10.1016/j.tet.2013.11.070

Reference yield:

(2R,3E)-4-[1-(benzyloxy)pent-3-en-2-yloxy]-1-(methoxymethoxy)-2-methylbenzene (1313708-39-2) → 6-[(2R,3E)-5-(benzyloxy)pent-3-en-2-yl]-2-[(2E)-4-hydroxy-4-methylpent-2-enyl]-4-(methoxymethoxy)-3-methylphenol (1528746-76-0)

Guidance literature:

Multi-step reaction with 7 steps

1: trimethylaluminum / hexane / 0.5 h / 0 - 20 °C / Inert atmosphere

2: potassium carbonate / acetonitrile / 4 h / 20 °C / Inert atmosphere

3: tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

5: tributylphosphine / tetrahydrofuran / 0.5 h / 20 °C

6: dihydrogen peroxide / tetrahydrofuran; water / 0.25 h / 60 °C

7: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 53 h / 110 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tributylphosphine; tetrabutyl ammonium fluoride; dihydrogen peroxide; trimethylaluminum; potassium carbonate; In tetrahydrofuran; hexane; water; toluene; acetonitrile;

DOI:10.1016/j.tet.2013.11.070

upstream raw materials:

(2R,3E)-2-[5-(benzyloxy)pent-3-en-2-yl]-4-(methoxymethoxy)-5-methylphenol

(2R,3E)-4-[1-(benzyloxy)pent-3-en-2-yloxy]-1-(methoxymethoxy)-2-methylbenzene

(2R)-methyl 2-{2-[(2R,3E)-5-(benzyloxy)pent-3-en-2-yl]-4-(methoxymethoxy)-5-methylphenoxy}-4-(tert-butyldiphenylsilyloxy)butanoate

(3R)-3-[2-(2R,3E)-5-benzyloxypent-3-en-2-yl-4-methoxymethoxy-5-methylphenoxy]-5-(tert-butyldiphenylsilyloxy)-2-methylpentan-2-ol

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