(R)-4-(3-Allyloxy-phenyl)-5-benzyloxy-3-oxo-pentanoic acid ethyl ester

Base Information

• Chemical Name: (R)-4-(3-Allyloxy-phenyl)-5-benzyloxy-3-oxo-pentanoic acid ethyl ester
• CAS No.: 155499-24-4
• Molecular Formula: C₂₃H₂₆O₅
• Molecular Weight: 382.456
• Mol file: 155499-24-4.mol

Synonyms:(R)-4-(3-Allyloxy-phenyl)-5-benzyloxy-3-oxo-pentanoic acid ethyl ester

Chemical Property of (R)-4-(3-Allyloxy-phenyl)-5-benzyloxy-3-oxo-pentanoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-(3-Allyloxy-phenyl)-5-benzyloxy-3-oxo-pentanoic acid ethyl ester

There total 22 articles about (R)-4-(3-Allyloxy-phenyl)-5-benzyloxy-3-oxo-pentanoic acid ethyl ester 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:

ethyl 3-hydroxyphenylacetate (22446-38-4) → (R)-4-(3-Allyloxy-phenyl)-5-benzyloxy-3-oxo-pentanoic acid ethyl ester (155499-24-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 96 percent / K₂CO₃ / 4 h / 55 °C

2: 90 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

3: 63 percent / DIBALH / CH₂Cl₂ / 0 °C / to room temperature

4: 3A molecular sieves / PPL / 24 h / 0 °C

5: p-TSA / CH₂Cl₂ / Ambient temperature

6: KOH / methanol / Ambient temperature

7: 98 percent / NaH / dimethylformamide / Ambient temperature

8: 93 percent / p-TSA / methanol / Ambient temperature

9: 90 percent / Jones reagent / acetone / 0 °C

10: 1.) CDI / 1.) THF, room temperature, 2.) -78 deg C

With potassium hydroxide; jones reagent; 3 A molecular sieve; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; 1,1'-carbonyldiimidazole; lithium diisopropyl amide; PPL; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(00)61382-5

Reference yield:

m-hydroxyphenylacetic acid (621-37-4) → (R)-4-(3-Allyloxy-phenyl)-5-benzyloxy-3-oxo-pentanoic acid ethyl ester (155499-24-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 94 percent / H₂SO₄ / Heating

2: 96 percent / K₂CO₃ / 4 h / 55 °C

3: 90 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

4: 63 percent / DIBALH / CH₂Cl₂ / 0 °C / to room temperature

5: 3A molecular sieves / PPL / 24 h / 0 °C

6: p-TSA / CH₂Cl₂ / Ambient temperature

7: KOH / methanol / Ambient temperature

8: 98 percent / NaH / dimethylformamide / Ambient temperature

9: 93 percent / p-TSA / methanol / Ambient temperature

10: 90 percent / Jones reagent / acetone / 0 °C

11: 1.) CDI / 1.) THF, room temperature, 2.) -78 deg C

With potassium hydroxide; jones reagent; 3 A molecular sieve; sulfuric acid; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; 1,1'-carbonyldiimidazole; lithium diisopropyl amide; PPL; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(00)61382-5

Reference yield:

3-allyloxyphenyl acetic acid ethyl ester (169888-83-9) → (R)-4-(3-Allyloxy-phenyl)-5-benzyloxy-3-oxo-pentanoic acid ethyl ester (155499-24-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 90 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

2: 63 percent / DIBALH / CH₂Cl₂ / 0 °C / to room temperature

3: 3A molecular sieves / PPL / 24 h / 0 °C

4: p-TSA / CH₂Cl₂ / Ambient temperature

5: KOH / methanol / Ambient temperature

6: 98 percent / NaH / dimethylformamide / Ambient temperature

7: 93 percent / p-TSA / methanol / Ambient temperature

8: 90 percent / Jones reagent / acetone / 0 °C

9: 1.) CDI / 1.) THF, room temperature, 2.) -78 deg C

With potassium hydroxide; jones reagent; 3 A molecular sieve; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,1'-carbonyldiimidazole; lithium diisopropyl amide; PPL; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(00)61382-5

upstream raw materials:

lithium 1-ethoxyethenolate

(R)-2-(3-Allyloxy-phenyl)-3-benzyloxy-propionic acid

(S)-2-<3-(allyloxy)phenyl>-3-(benzyloxy)propanoic acid

m-hydroxyphenylacetic acid

Downstream raw materials:

{2-[(R)-2-Benzyloxy-1-(3-hydroxy-phenyl)-ethyl]-[1,3]dithiolan-2-yl}-acetic acid ethyl ester