5(S),12(S)-dihydroxy-13-phenoxy-6(Z),8(E),10(E)-tridecatrienoic acid

Base Information

• Chemical Name: 5(S),12(S)-dihydroxy-13-phenoxy-6(Z),8(E),10(E)-tridecatrienoic acid
• CAS No.: 129594-52-1
• Molecular Formula: C₁₉H₂₄O₅
• Molecular Weight: 332.397
• Mol file: 129594-52-1.mol

Synonyms:

Chemical Property of 5(S),12(S)-dihydroxy-13-phenoxy-6(Z),8(E),10(E)-tridecatrienoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5(S),12(S)-dihydroxy-13-phenoxy-6(Z),8(E),10(E)-tridecatrienoic acid

There total 14 articles about 5(S),12(S)-dihydroxy-13-phenoxy-6(Z),8(E),10(E)-tridecatrienoic 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:

allyl phenyl ether (1746-13-0) → 5(S),12(S)-dihydroxy-13-phenoxy-6(Z),8(E),10(E)-tridecatrienoic acid (129594-52-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) O₃, 2) dimethyl sulfide / 1) MeOH, -78 deg C, 2) -78 deg C to RT, 1.5h

2: 1) MeLi / 1) Et₂O, 0 deg C, 30 min, 2) 0 deg C, 30 min

3: 95 percent / <(CH₃O(CH₂)2O)2AlH₂>Na / toluene / Heating

4: 47 percent / t-BuOOH, Ti(O-i-Pr)4, L-(+)-DIPT, molecular sieves 4 Angstroem / CH₂Cl₂

6: 1) disiamylborane, 2) 2N LiOH / 2) Pd(PPh₃)4 / 1) THF, 2) THF

7: 84 percent / n-Bu₄NF / tetrahydrofuran

With titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium hydroxide; dimethylsulfide; L-(+)-diisopropyl tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; methyllithium; bis-(1,2-dimethylpropyl)borane; ozone; sodium bis(2-methoxyethoxy)aluminium dihydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/jo00306a007

Reference yield:

methyl 4-formylbutanoate (6026-86-4) → 5(S),12(S)-dihydroxy-13-phenoxy-6(Z),8(E),10(E)-tridecatrienoic acid (129594-52-1)

Guidance literature:

Multi-step reaction with 9 steps

2: 43 percent / t-BuOOH, Ti(O-i-Pr)4, D-(-)-DIPT, molecular sieves 4 Angstroem / CH₂Cl₂ / 21 h / -21 °C

3: Br₂ / CH₂Cl₂ / 0.17 h / -70 °C

4: n-Bu₄NF / tetrahydrofuran / 0.25 h / -70 °C

5: imidazole / dimethylformamide / 5 h / Ambient temperature

6: n-PrNH₂ / Pd(PPh₃)4, CuI / benzene / 20 h / Ambient temperature

7: 1) AgNO₃, 2) KCN / 1) THF, EtOH, H₂O, 0 deg C, 30 min, 2) 0 deg C, 30 min

8: 1) disiamylborane, 2) 2N LiOH / 2) Pd(PPh₃)4 / 1) THF, 2) THF

9: 84 percent / n-Bu₄NF / tetrahydrofuran

With 1H-imidazole; titanium(IV) isopropylate; propylamine; tert.-butylhydroperoxide; potassium cyanide; lithium hydroxide; 4 A molecular sieve; tetrabutyl ammonium fluoride; bromine; bis-(1,2-dimethylpropyl)borane; D-(-)-diisopropyl tartrate; silver nitrate; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00306a007

Reference yield:

(Z)-(S)-7-Bromo-5-hydroxy-hept-6-enoic acid methyl ester (111037-32-2) → 5(S),12(S)-dihydroxy-13-phenoxy-6(Z),8(E),10(E)-tridecatrienoic acid (129594-52-1)

Guidance literature:

Multi-step reaction with 5 steps

1: imidazole / dimethylformamide / 5 h / Ambient temperature

2: n-PrNH₂ / Pd(PPh₃)4, CuI / benzene / 20 h / Ambient temperature

3: 1) AgNO₃, 2) KCN / 1) THF, EtOH, H₂O, 0 deg C, 30 min, 2) 0 deg C, 30 min

4: 1) disiamylborane, 2) 2N LiOH / 2) Pd(PPh₃)4 / 1) THF, 2) THF

5: 84 percent / n-Bu₄NF / tetrahydrofuran

With 1H-imidazole; propylamine; potassium cyanide; lithium hydroxide; tetrabutyl ammonium fluoride; bis-(1,2-dimethylpropyl)borane; silver nitrate; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00306a007

upstream raw materials:

methyl 4-formylbutanoate

allyl phenyl ether

(Z)-(S)-7-Bromo-5-hydroxy-hept-6-enoic acid methyl ester

1-phenoxy-4-(trimethylsilyl)-3-butyn-2-ol