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

Base Information

• Chemical Name: {2-[(R)-2-Benzyloxy-1-(3-hydroxy-phenyl)-ethyl]-[1,3]dithiolan-2-yl}-acetic acid ethyl ester
• CAS No.: 155499-26-6
• Molecular Formula: C₂₂H₂₆O₄S₂
• Molecular Weight: 418.578
• Mol file: 155499-26-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 24 articles about {2-[(R)-2-Benzyloxy-1-(3-hydroxy-phenyl)-ethyl]-[1,3]dithiolan-2-yl}-acetic 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: 80.0%

ethane-1,2-dithiol (540-63-6) + (R)-5-Benzyloxy-4-(3-hydroxy-phenyl)-3-oxo-pentanoic acid ethyl ester → {2-[(R)-2-Benzyloxy-1-(3-hydroxy-phenyl)-ethyl]-[1,3]dithiolan-2-yl}-acetic acid ethyl ester (155499-26-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In tetrahydrofuran; dichloromethane; Ambient temperature;

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

Reference yield:

m-hydroxyphenylacetic acid (621-37-4) → {2-[(R)-2-Benzyloxy-1-(3-hydroxy-phenyl)-ethyl]-[1,3]dithiolan-2-yl}-acetic acid ethyl ester (155499-26-6)

Guidance literature:

Multi-step reaction with 13 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

13: 80 percent / trimethylsilyl triflate, 4A molecular sieves / CH₂Cl₂; tetrahydrofuran / Ambient temperature

With potassium hydroxide; jones reagent; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 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

Reference yield:

ethyl 3-hydroxyphenylacetate (22446-38-4) → {2-[(R)-2-Benzyloxy-1-(3-hydroxy-phenyl)-ethyl]-[1,3]dithiolan-2-yl}-acetic acid ethyl ester (155499-26-6)

Guidance literature:

Multi-step reaction with 12 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

12: 80 percent / trimethylsilyl triflate, 4A molecular sieves / CH₂Cl₂; tetrahydrofuran / Ambient temperature

With potassium hydroxide; jones reagent; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 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

upstream raw materials:

ethane-1,2-dithiol

m-hydroxyphenylacetic acid

ethyl 3-hydroxyphenylacetate

benzyl bromide