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

Base Information

• Chemical Name: Benzoic acid (2Z,4E,6E)-(1S,8S)-8-(tert-butyl-diphenyl-silanyloxy)-9,9-difluoro-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,6-trien-10-ynyl ester
• CAS No.: 120623-85-0
• Molecular Formula: C₄₄H₅₂F₂O₅Si
• Molecular Weight: 726.976
• Mol file: 120623-85-0.mol

Synonyms:

Chemical Property of Benzoic acid (2Z,4E,6E)-(1S,8S)-8-(tert-butyl-diphenyl-silanyloxy)-9,9-difluoro-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,6-trien-10-ynyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2Z,4E,6E)-(1S,8S)-8-(tert-butyl-diphenyl-silanyloxy)-9,9-difluoro-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,6-trien-10-ynyl ester

There total 10 articles about Benzoic acid (2Z,4E,6E)-(1S,8S)-8-(tert-butyl-diphenyl-silanyloxy)-9,9-difluoro-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,6-trien-10-ynyl 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:

2-Oxo-non-3-ynoic acid ethyl ester (120623-87-2) → Benzoic acid (2Z,4E,6E)-(1S,8S)-8-(tert-butyl-diphenyl-silanyloxy)-9,9-difluoro-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,6-trien-10-ynyl ester (120623-85-0)

Guidance literature:

Multi-step reaction with 9 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

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

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

Reference yield:

2,2-Difluoro-non-3-ynoic acid ethyl ester (120623-79-2) → Benzoic acid (2Z,4E,6E)-(1S,8S)-8-(tert-butyl-diphenyl-silanyloxy)-9,9-difluoro-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,6-trien-10-ynyl ester (120623-85-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 79 percent / n-BuLi / tetrahydrofuran / -78 °C

2: 72 percent / R-Alpine Borane

3: 75 percent / Red-Al / tetrahydrofuran

4: 74 percent / imidazole / dimethylformamide

5: 84 percent / AcOH, water / tetrahydrofuran

6: 91 percent / CBr₄, DIPHOS

7: 80 percent / acetonitrile

8: nBuLi / tetrahydrofuran; hexamethylphosphoric acid triamide

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

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

Reference yield:

(E)-7,7-Difluoro-1-(tetrahydro-pyran-2-yloxy)-tetradec-2-ene-4,8-diyn-6-one (120623-80-5) → Benzoic acid (2Z,4E,6E)-(1S,8S)-8-(tert-butyl-diphenyl-silanyloxy)-9,9-difluoro-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,6-trien-10-ynyl ester (120623-85-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 72 percent / R-Alpine Borane

2: 75 percent / Red-Al / tetrahydrofuran

3: 74 percent / imidazole / dimethylformamide

4: 84 percent / AcOH, water / tetrahydrofuran

5: 91 percent / CBr₄, DIPHOS

6: 80 percent / acetonitrile

7: nBuLi / tetrahydrofuran; hexamethylphosphoric acid triamide

With 1H-imidazole; n-butyllithium; B-isopinocampheyl-9-borabicyclo[3.3.1]nonane; carbon tetrabromide; temephos; water; acetic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; 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:

Methyl 5S-benzoyloxy-5-formylvalerate

[(2E,4E)-(S)-6-(tert-Butyl-diphenyl-silanyloxy)-7,7-difluoro-tetradeca-2,4-dien-8-ynyl]-triphenyl-phosphonium; bromide

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

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

Downstream raw materials:

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

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