dimethyl (2'E,1'S)-2-(4'-acetoxy-3'-buten-2'-yl)-2-benzylmalonate

Base Information

• Chemical Name: dimethyl (2'E,1'S)-2-(4'-acetoxy-3'-buten-2'-yl)-2-benzylmalonate
• CAS No.: 342906-95-0
• Molecular Formula: C₁₈H₂₂O₆
• Molecular Weight: 334.369
• Mol file: 342906-95-0.mol

Synonyms:dimethyl (2'E,1'S)-2-(4'-acetoxy-3'-buten-2'-yl)-2-benzylmalonate

Chemical Property of dimethyl (2'E,1'S)-2-(4'-acetoxy-3'-buten-2'-yl)-2-benzylmalonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl (2'E,1'S)-2-(4'-acetoxy-3'-buten-2'-yl)-2-benzylmalonate

There total 1 articles about dimethyl (2'E,1'S)-2-(4'-acetoxy-3'-buten-2'-yl)-2-benzylmalonate 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:

1,1-diacetoxy-but-2-ene (78267-54-6,5860-35-5) + dimethyl sodiobenzylmalonate → dimethyl (2'E,1'S)-2-(1'-acetoxy-2'-butenyl)-2-benzylmalonate + dimethyl (2'E,1'R)-2-(1'-acetoxy-2'-butenyl)-2-benzylmalonate + 2-((E)-(R)-3-Acetoxy-1-methyl-allyl)-2-benzyl-malonic acid dimethyl ester + dimethyl (2'E,1'S)-2-(4'-acetoxy-3'-buten-2'-yl)-2-benzylmalonate (342906-95-0)

Guidance literature:

With bis(η3-allyl-μ-chloropalladium(II)); (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; In tetrahydrofuran; at 25 ℃; for 3h; Title compound not separated from byproducts.;

DOI:10.1021/ja003774o

Reference yield:

dimethyl (2'E,1'S)-2-(4'-acetoxy-3'-buten-2'-yl)-2-benzylmalonate (342906-95-0) → (S)-methylbenzyl (R)-3-methyl-4,4-bis(methoxycarbonyl)-5-phenylpentanamide

Guidance literature:

Multi-step reaction with 3 steps

1: p-toluenesulfonic acid monohydrate / methanol / 10 h / 65 °C

2: 86 percent / CrO₃; aq. H₂SO₄ / acetone / 1 h / 20 °C

3: 2-chloro-1-methylpyridinium iodide; triethylamine / CH₂Cl₂ / 15 h / 25 °C

With chromium(VI) oxide; sulfuric acid; 2-chloro-1-methyl-pyridinium iodide; toluene-4-sulfonic acid; triethylamine; In methanol; dichloromethane; acetone; 2: Jones oxidation;

DOI:10.1021/ja003774o

Reference yield:

dimethyl (2'E,1'S)-2-(4'-acetoxy-3'-buten-2'-yl)-2-benzylmalonate (342906-95-0) → (3S)-3-methyl-4,4-bis(methoxycarbonyl)-5-phenylpentanoic acid (342906-99-4)

Guidance literature:

Multi-step reaction with 2 steps

1: p-toluenesulfonic acid monohydrate / methanol / 10 h / 65 °C

2: 86 percent / CrO₃; aq. H₂SO₄ / acetone / 1 h / 20 °C

With chromium(VI) oxide; sulfuric acid; toluene-4-sulfonic acid; In methanol; acetone; 2: Jones oxidation;

DOI:10.1021/ja003774o

upstream raw materials:

1,1-diacetoxy-but-2-ene

Downstream raw materials:

dimethyl (2'S)-2-(4',4'-dimethoxy-but-2'-yl)-2-benzylmalonate

(3S)-3-methyl-4,4-bis(methoxycarbonyl)-5-phenylpentanoic acid