(2S,3S)-methyl 3-hydroxy-2-methyl-2-((R)-1-phenylallyl)hept-6-enoate

Base Information

• Chemical Name: (2S,3S)-methyl 3-hydroxy-2-methyl-2-((R)-1-phenylallyl)hept-6-enoate
• CAS No.: 1598415-25-8
• Molecular Formula: C₁₈H₂₄O₃
• Molecular Weight: 288.387
• Mol file: 1598415-25-8.mol

Synonyms:

Chemical Property of (2S,3S)-methyl 3-hydroxy-2-methyl-2-((R)-1-phenylallyl)hept-6-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-methyl 3-hydroxy-2-methyl-2-((R)-1-phenylallyl)hept-6-enoate

There total 5 articles about (2S,3S)-methyl 3-hydroxy-2-methyl-2-((R)-1-phenylallyl)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:

4-pentenal (2100-17-6) → (2S,3S)-methyl 3-hydroxy-2-methyl-2-((R)-1-phenylallyl)hept-6-enoate (1598415-25-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: titanium tetrachloride / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

1.2: 0.67 h / 0 °C / Inert atmosphere

1.3: -78 - -20 °C / Inert atmosphere

2.1: 1H-imidazole; dmap / dichloromethane

3.1: lithium hexamethyldisilazane / tetrahydrofuran; toluene / -78 - 25 °C / Inert atmosphere

3.2: Inert atmosphere

4.1: diethyl ether / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; titanium tetrachloride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 1.1: |Aldol Condensation / 1.2: |Aldol Condensation / 1.3: |Aldol Condensation / 3.1: |Claisen-Ireland Rearrangement;

DOI:10.1021/ol5008422

Reference yield:

(2R,3S)-cinnamyl 3-hydroxy-2-methylhept-6-enoate → (2S,3S)-methyl 3-hydroxy-2-methyl-2-((R)-1-phenylallyl)hept-6-enoate (1598415-25-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran; toluene / -78 - 25 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: diethyl ether / 20 °C / Inert atmosphere

With lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; toluene; 1.1: |Claisen-Ireland Rearrangement;

DOI:10.1021/ol5008422

Reference yield:

hex-5-ene-1,2-diol (36842-44-1) → (2S,3S)-methyl 3-hydroxy-2-methyl-2-((R)-1-phenylallyl)hept-6-enoate (1598415-25-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium periodate / dichloromethane; water

2.1: titanium tetrachloride / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

2.2: 0.67 h / 0 °C / Inert atmosphere

2.3: -78 - -20 °C / Inert atmosphere

3.1: 1H-imidazole; dmap / dichloromethane

4.1: lithium hexamethyldisilazane / tetrahydrofuran; toluene / -78 - 25 °C / Inert atmosphere

4.2: Inert atmosphere

5.1: diethyl ether / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; sodium periodate; titanium tetrachloride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene; 2.1: |Aldol Condensation / 2.2: |Aldol Condensation / 2.3: |Aldol Condensation / 4.1: |Claisen-Ireland Rearrangement;

DOI:10.1021/ol5008422

upstream raw materials:

4-pentenal

hex-5-ene-1,2-diol

diazomethane

(2R,3S)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-2-methylhept-6-en-1-one