3-(2-{(3S)-4-hydroxy-3-[(4-methoxybenzyl)oxy]-1-butynyl}phenyl)propanoic acid

Base Information

• Chemical Name: 3-(2-{(3S)-4-hydroxy-3-[(4-methoxybenzyl)oxy]-1-butynyl}phenyl)propanoic acid
• CAS No.: 1318793-13-3
• Molecular Formula: C₂₁H₂₂O₅
• Molecular Weight: 354.403
• Mol file: 1318793-13-3.mol

Synonyms:3-(2-{(3S)-4-hydroxy-3-[(4-methoxybenzyl)oxy]-1-butynyl}phenyl)propanoic acid

Chemical Property of 3-(2-{(3S)-4-hydroxy-3-[(4-methoxybenzyl)oxy]-1-butynyl}phenyl)propanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(2-{(3S)-4-hydroxy-3-[(4-methoxybenzyl)oxy]-1-butynyl}phenyl)propanoic acid

There total 8 articles about 3-(2-{(3S)-4-hydroxy-3-[(4-methoxybenzyl)oxy]-1-butynyl}phenyl)propanoic acid 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: 100.0%

methyl 3-(2-{(3S)-4-hydroxy-3-[(4-methoxybenzyl)oxy]-1-butynyl}phenyl)propanoate (1318793-10-0) → 3-(2-{(3S)-4-hydroxy-3-[(4-methoxybenzyl)oxy]-1-butynyl}phenyl)propanoic acid (1318793-13-3)

Guidance literature:

methyl 3-(2-{(3S)-4-hydroxy-3-[(4-methoxybenzyl)oxy]-1-butynyl}phenyl)propanoate; With lithium hydroxide monohydrate; In methanol; at 20 ℃; for 18h;

With hydrogenchloride; In methanol; water; pH=7;

DOI:10.1016/j.tetlet.2011.06.024

Reference yield:

methyl 3-(2-iodophenyl)propanoate (141273-91-8) → 3-(2-{(3S)-4-hydroxy-3-[(4-methoxybenzyl)oxy]-1-butynyl}phenyl)propanoic acid (1318793-13-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / 19 h / 20 °C

2.1: water / methanol / 22 h / 20 - 80 °C

3.1: 1H-imidazole / dichloromethane; N,N-dimethyl-formamide / 4 h / 0 - 20 °C

4.1: trifluorormethanesulfonic acid / diethyl ether / 20 h / 0 - 20 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2.5 h / 20 °C

6.1: lithium hydroxide monohydrate / methanol / 18 h / 20 °C

6.2: pH 7

With 1H-imidazole; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium hydroxide monohydrate; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; water; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1.1: Sonogashira coupling;

DOI:10.1016/j.tetlet.2011.06.024

Reference yield:

methyl 3-(2-{2-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]ethynyl}phenyl)propanoate (1318792-98-1) → 3-(2-{(3S)-4-hydroxy-3-[(4-methoxybenzyl)oxy]-1-butynyl}phenyl)propanoic acid (1318793-13-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: water / methanol / 22 h / 20 - 80 °C

2.1: 1H-imidazole / dichloromethane; N,N-dimethyl-formamide / 4 h / 0 - 20 °C

3.1: trifluorormethanesulfonic acid / diethyl ether / 20 h / 0 - 20 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2.5 h / 20 °C

5.1: lithium hydroxide monohydrate / methanol / 18 h / 20 °C

5.2: pH 7

With 1H-imidazole; lithium hydroxide monohydrate; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; water; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2011.06.024

upstream raw materials:

methyl 3-(2-iodophenyl)propanoate

methyl 3-(2-{2-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]ethynyl}phenyl)propanoate

methyl 3-{2-[(3S)-3,4-dihydroxy-1-butynyl]phenyl}propanoate

methyl 3-[2-((3S)-4-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-3-hydroxy-1-butynyl)phenyl]propanoate

Downstream raw materials:

(6S)-6-[(4-methoxybenzyl)oxy]-7,8-didehydro-1,2,5,6-tetrahydro-3H-4-benzoxecin-3-one