(4R*)-Methyl 4-(benzyloxy)-2--5-methyl-(2E)-hexenoate

Base Information

• Chemical Name: (4R*)-Methyl 4-(benzyloxy)-2--5-methyl-(2E)-hexenoate
• CAS No.: 149287-50-3
• Molecular Formula: C₁₇H₂₃NO₅
• Molecular Weight: 321.373
• Mol file: 149287-50-3.mol

Synonyms:

Chemical Property of (4R*)-Methyl 4-(benzyloxy)-2--5-methyl-(2E)-hexenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R*)-Methyl 4-(benzyloxy)-2--5-methyl-(2E)-hexenoate

There total 7 articles about (4R*)-Methyl 4-(benzyloxy)-2--5-methyl-(2E)-hexenoate 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:

2-(Benzyloxy)-3-methylbutanal (96925-01-8) + Methyl 2-(dimethoxyphosphinyl)-2-ethanoate (144001-86-5) → (4R*)-Methyl 4-(benzyloxy)-2--5-methyl-(2E)-hexenoate (149287-50-3) + (4R*)-Methyl 4-(benzyloxy)-2--5-methyl-(2Z)-hexenoate (149287-49-0)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 1h; Yield given. Yields of byproduct given;

DOI:10.1021/jo00068a047

Reference yield:

methyl 2-hydroxy-3-methylbutanoate (17417-00-4) → (4R*)-Methyl 4-(benzyloxy)-2--5-methyl-(2E)-hexenoate (149287-50-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) NaH, 2) nBu₄NI / 1) THF, 0 deg C, 15 min, 2) 0 to 24 deg C, 30 min

2: 92 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

3: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 2) to 0 deg c

4: iPr₂NLi / tetrahydrofuran / 1 h / -78 °C

With lithium aluminium tetrahydride; oxalyl dichloride; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/jo00068a047

Reference yield:

2-hydroxy-3-methylbutanoic acid (4026-18-0,17407-55-5,17407-56-6,600-37-3) → (4R*)-Methyl 4-(benzyloxy)-2--5-methyl-(2E)-hexenoate (149287-50-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / diethyl ether / 24 °C

2: 1) NaH, 2) nBu₄NI / 1) THF, 0 deg C, 15 min, 2) 0 to 24 deg C, 30 min

3: 92 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

4: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 2) to 0 deg c

5: iPr₂NLi / tetrahydrofuran / 1 h / -78 °C

With lithium aluminium tetrahydride; oxalyl dichloride; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether;

DOI:10.1021/jo00068a047

upstream raw materials:

2-(Benzyloxy)-3-methylbutanal

Methyl 2-(dimethoxyphosphinyl)-2-ethanoate

methyl 2-hydroxy-3-methylbutanoate

2-hydroxy-3-methylbutanoic acid