Benzoic acid (2Z,4E,6E,10Z)-(1S,8S)-9,9-difluoro-8-hydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,6,10-tetraenyl ester

Base Information

• Chemical Name: Benzoic acid (2Z,4E,6E,10Z)-(1S,8S)-9,9-difluoro-8-hydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,6,10-tetraenyl ester
• CAS No.: 120642-26-4
• Molecular Formula: C₂₈H₃₆F₂O₅
• Molecular Weight: 490.588
• Mol file: 120642-26-4.mol

Synonyms:

Chemical Property of Benzoic acid (2Z,4E,6E,10Z)-(1S,8S)-9,9-difluoro-8-hydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,6,10-tetraenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2Z,4E,6E,10Z)-(1S,8S)-9,9-difluoro-8-hydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,6,10-tetraenyl ester

There total 12 articles about Benzoic acid (2Z,4E,6E,10Z)-(1S,8S)-9,9-difluoro-8-hydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,6,10-tetraenyl 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: 44.0%

Benzoic acid (2Z,4E,6E)-(1S,8S)-9,9-difluoro-8-hydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,6-trien-10-ynyl ester (120623-86-1) → Benzoic acid (2Z,4E,6E,10Z)-(1S,8S)-9,9-difluoro-8-hydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,6,10-tetraenyl ester (120642-26-4)

Guidance literature:

With hydrogen; Lindlar catalyst;

DOI:10.1016/S0040-4039(00)80840-0

Reference yield:

Methyl 5S-benzoyloxy-5-formylvalerate (76745-20-5) → Benzoic acid (2Z,4E,6E,10Z)-(1S,8S)-9,9-difluoro-8-hydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,6,10-tetraenyl ester (120642-26-4)

Guidance literature:

Multi-step reaction with 3 steps

1: nBuLi / tetrahydrofuran; hexamethylphosphoric acid triamide

2: 51 percent / nBu₄NF / tetrahydrofuran

3: 44 percent / H₂ / Pd-BaSO₄-quinoline

With n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; Lindlar catalyst; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1016/S0040-4039(00)80840-0

Reference yield:

2-Oxo-non-3-ynoic acid ethyl ester (120623-87-2) → Benzoic acid (2Z,4E,6E,10Z)-(1S,8S)-9,9-difluoro-8-hydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,6,10-tetraenyl ester (120642-26-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 75 percent / diethylaminosulfur trifluoride

2: 79 percent / n-BuLi / tetrahydrofuran / -78 °C

3: 72 percent / R-Alpine Borane

4: 75 percent / Red-Al / tetrahydrofuran

5: 74 percent / imidazole / dimethylformamide

6: 84 percent / AcOH, water / tetrahydrofuran

7: 91 percent / CBr₄, DIPHOS

8: 80 percent / acetonitrile

9: nBuLi / tetrahydrofuran; hexamethylphosphoric acid triamide

10: 51 percent / nBu₄NF / tetrahydrofuran

11: 44 percent / H₂ / Pd-BaSO₄-quinoline

With 1H-imidazole; n-butyllithium; B-isopinocampheyl-9-borabicyclo[3.3.1]nonane; carbon tetrabromide; diethylamino-sulfur trifluoride; temephos; tetrabutyl ammonium fluoride; water; hydrogen; acetic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; Lindlar catalyst; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(00)80840-0

upstream raw materials:

Benzoic acid (2Z,4E,6E)-(1S,8S)-9,9-difluoro-8-hydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,6-trien-10-ynyl ester

Methyl 5S-benzoyloxy-5-formylvalerate

2-Oxo-non-3-ynoic acid ethyl ester

2,2-Difluoro-non-3-ynoic acid ethyl ester