(4R,5S,6R,Z)-5-hydroxy-6-methoxy-2,4-dimethylocta-2,7-dienyl hept-6-enoate

Base Information

• Chemical Name: (4R,5S,6R,Z)-5-hydroxy-6-methoxy-2,4-dimethylocta-2,7-dienyl hept-6-enoate
• CAS No.: 1262138-02-2
• Molecular Formula: C₁₈H₃₀O₄
• Molecular Weight: 310.434
• Mol file: 1262138-02-2.mol

Synonyms:

Chemical Property of (4R,5S,6R,Z)-5-hydroxy-6-methoxy-2,4-dimethylocta-2,7-dienyl hept-6-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S,6R,Z)-5-hydroxy-6-methoxy-2,4-dimethylocta-2,7-dienyl hept-6-enoate

There total 15 articles about (4R,5S,6R,Z)-5-hydroxy-6-methoxy-2,4-dimethylocta-2,7-dienyl hept-6-enoate 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: 73.0%

(4R,5S,6R,Z)-5-[(tert-butyldimethylsilyl)oxy]-6-methoxy-2,4-dimethylocta-2,7-dienyl hept-6-enoate (1262137-99-4) → (4R,5S,6R,Z)-5-hydroxy-6-methoxy-2,4-dimethylocta-2,7-dienyl hept-6-enoate (1262138-02-2)

Guidance literature:

With hydrogen fluoride; In dichloromethane; water; acetonitrile; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1002/ejoc.201001097

Reference yield:

<4S,3(2S,3R)>-4-benzyl-3-(3-hydroxy-2-methyl-4-pentenoyl)-2-oxazolidinone (139426-88-3) → (4R,5S,6R,Z)-5-hydroxy-6-methoxy-2,4-dimethylocta-2,7-dienyl hept-6-enoate (1262138-02-2)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 0.33 h / 0 °C / Inert atmosphere

2.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone / 10 h / 20 °C / Inert atmosphere

3.1: 10-camphorsufonic acid / dichloromethane / 12 h / 20 °C / Inert atmosphere

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

5.1: 1H-imidazole / dichloromethane / 1 h / 0 °C / Inert atmosphere

6.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 12 h / 20 °C / Inert atmosphere; Darkness

7.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2 h / 20 °C / Inert atmosphere

8.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve

9.1: toluene / 4 h / 60 °C / Inert atmosphere; Darkness

10.1: pyridine; hydrogen fluoride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere

11.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

12.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

12.2: 12 h / 20 °C / Inert atmosphere

13.1: diisobutylaluminium hydride / dichloromethane; toluene / -15 - 20 °C / Inert atmosphere

14.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 12 h / 20 °C / Inert atmosphere

15.1: hydrogen fluoride / dichloromethane; water; acetonitrile / 24 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; 10-camphorsufonic acid; hydrogen fluoride; water; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; acetone; toluene; acetonitrile;

DOI:10.1002/ejoc.201001097

Reference yield:

(S)-4-benzyl-3-{(2S,3R)-3-[(tert-butyldimethylsilyl)oxy]-2-methylpent-4-enoyl}oxazolidin-2-one (519176-52-4) → (4R,5S,6R,Z)-5-hydroxy-6-methoxy-2,4-dimethylocta-2,7-dienyl hept-6-enoate (1262138-02-2)

Guidance literature:

Multi-step reaction with 14 steps

1.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone / 10 h / 20 °C / Inert atmosphere

2.1: 10-camphorsufonic acid / dichloromethane / 12 h / 20 °C / Inert atmosphere

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

4.1: 1H-imidazole / dichloromethane / 1 h / 0 °C / Inert atmosphere

5.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 12 h / 20 °C / Inert atmosphere; Darkness

6.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2 h / 20 °C / Inert atmosphere

7.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve

8.1: toluene / 4 h / 60 °C / Inert atmosphere; Darkness

9.1: pyridine; hydrogen fluoride / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere

10.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

11.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

11.2: 12 h / 20 °C / Inert atmosphere

12.1: diisobutylaluminium hydride / dichloromethane; toluene / -15 - 20 °C / Inert atmosphere

13.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 12 h / 20 °C / Inert atmosphere

14.1: hydrogen fluoride / dichloromethane; water; acetonitrile / 24 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; 10-camphorsufonic acid; hydrogen fluoride; water; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; acetone; toluene; acetonitrile;

DOI:10.1002/ejoc.201001097

upstream raw materials:

(3S,4S,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(((4-methoxybenzyl)oxy)methyl)-3-methyldihydrofuran-2(3H)-one

(2R,3S,4R)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2-methylpentane-1,4-diol

(2R,3S,4R)-3,5-bis((tert-butyldimethylsilyl)oxy)-1-((4-methoxybenzyl)oxy)-4-methylpentan-2-ol

(2R,3S,4R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-2-methoxy-4-methylpentan-1-ol