(S)-ethyl 5-benzyloxy-4-<3-(hydroxy)phenyl>-3-oxopentanoate

Base Information

• Chemical Name: (S)-ethyl 5-benzyloxy-4-<3-(hydroxy)phenyl>-3-oxopentanoate
• CAS No.: 183800-18-2
• Molecular Formula: C₂₀H₂₂O₅
• Molecular Weight: 342.392
• Mol file: 183800-18-2.mol

Synonyms:(S)-ethyl 5-benzyloxy-4-<3-(hydroxy)phenyl>-3-oxopentanoate

Chemical Property of (S)-ethyl 5-benzyloxy-4-<3-(hydroxy)phenyl>-3-oxopentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-ethyl 5-benzyloxy-4-<3-(hydroxy)phenyl>-3-oxopentanoate

There total 24 articles about (S)-ethyl 5-benzyloxy-4-<3-(hydroxy)phenyl>-3-oxopentanoate 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: 81.0%

(S)-ethyl 4-<3-(allyloxy)phenyl>-5-benzyloxy-3-oxopentanoate (155499-23-3) → (S)-ethyl 5-benzyloxy-4-<3-(hydroxy)phenyl>-3-oxopentanoate (183800-18-2)

Guidance literature:

With tri-n-butyl-tin hydride; acetic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; Ambient temperature;

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

Reference yield:

ethyl 3-hydroxyphenylacetate (22446-38-4) → (S)-ethyl 5-benzyloxy-4-<3-(hydroxy)phenyl>-3-oxopentanoate (183800-18-2)

Guidance literature:

Multi-step reaction with 11 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

11: 81 percent / Bu₃SnH, AcOH / Pd(PPh₃)4 / toluene / Ambient temperature

With potassium hydroxide; jones reagent; 3 A molecular sieve; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; 1,1'-carbonyldiimidazole; lithium diisopropyl amide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

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

Reference yield:

m-hydroxyphenylacetic acid (621-37-4) → (S)-ethyl 5-benzyloxy-4-<3-(hydroxy)phenyl>-3-oxopentanoate (183800-18-2)

Guidance literature:

Multi-step reaction with 12 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

12: 81 percent / Bu₃SnH, AcOH / Pd(PPh₃)4 / toluene / Ambient temperature

With potassium hydroxide; jones reagent; 3 A molecular sieve; sulfuric acid; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; 1,1'-carbonyldiimidazole; lithium diisopropyl amide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

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

upstream raw materials:

(S)-ethyl 4-<3-(allyloxy)phenyl>-5-benzyloxy-3-oxopentanoate

(R)-3-acetoxy-2-<(3-allyloxy)phenyl>propan-1-ol

(R)-2-<3-(allyloxy)phenyl>-3-(benzyloxy)propan-1-ol

(S)-2-<3-(allyloxy)phenyl>-3-<(tetrahydropyran-2-yl)oxy>propan-1-ol

Downstream raw materials:

(S)-ethyl 5-benzyloxy-3,3-ethylendithio-4-<3-(hydroxy)phenyl>pentanoate