Benzoic acid (2E,4E,10Z)-(1S,8S)-8-(tert-butyl-diphenyl-silanyloxy)-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,10-trienyl ester

Base Information

Chemical Name:Benzoic acid (2E,4E,10Z)-(1S,8S)-8-(tert-butyl-diphenyl-silanyloxy)-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,10-trienyl ester
CAS No.:122221-81-2
Molecular Formula:C₄₄H₅₈O₅Si
Molecular Weight:695.027
Hs Code.:

Synonyms:Benzoic acid (2E,4E,10Z)-(1S,8S)-8-(tert-butyl-diphenyl-silanyloxy)-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,10-trienyl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

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

There total 11 articles about Benzoic acid (2E,4E,10Z)-(1S,8S)-8-(tert-butyl-diphenyl-silanyloxy)-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,10-trienyl 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: 14.0%

: 76745-20-5
Methyl 5S-benzoyloxy-5-formylvalerate

: 122221-78-7
[(2E,8Z)-(S)-6-(tert-Butyl-diphenyl-silanyloxy)-tetradeca-2,8-dienyl]-triphenyl-phosphonium

: 122221-80-1
Benzoic acid (2Z,4E,10Z)-(1S,8S)-8-(tert-butyl-diphenyl-silanyloxy)-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,10-trienyl ester

: 122221-81-2
Benzoic acid (2E,4E,10Z)-(1S,8S)-8-(tert-butyl-diphenyl-silanyloxy)-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,10-trienyl ester

Guidance literature:: With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1) -78 deg C, 1 h, 2) -78 to -50 deg C, 1.5 h;
DOI:10.1016/S0040-4039(00)95219-5

Reference yield:

: 32780-06-6
(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

: 122221-81-2
Benzoic acid (2E,4E,10Z)-(1S,8S)-8-(tert-butyl-diphenyl-silanyloxy)-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,10-trienyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: pyridine; CH₂Cl₂ / 6 h / 24 °C

2: NaOMe / 0.33 h

3: 79 percent / n-BuLi, CuCN / diethyl ether / -70 - -50 °C

4: DIBAL-H / toluene / 3 h / -78 °C

5: toluene / 15 h / 23 °C

6: DMAP, Et₃N / pyridine / 26 h / 45 °C

7: DIBAL-H / toluene / 1 h / -78 °C

8: CBr₄, PPh₃ / CH₂Cl₂ / 1 h

9: Ph₃P / acetonitrile / 6 h

10: 14 percent / 1) n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1) -78 deg C, 1 h, 2) -78 to -50 deg C, 1.5 h

With dmap; n-butyllithium; carbon tetrabromide; sodium methylate; diisobutylaluminium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; toluene; acetonitrile;
DOI:10.1016/S0040-4039(00)95219-5

Reference yield:

: 21461-84-7
(2S)-tetrahydro-5-oxofuran-2-carboxylic acid

: 122221-81-2
Benzoic acid (2E,4E,10Z)-(1S,8S)-8-(tert-butyl-diphenyl-silanyloxy)-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,10-trienyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: BH₃*Me₂S / tetrahydrofuran / 2 h / 0 - 23 °C

2: pyridine; CH₂Cl₂ / 6 h / 24 °C

3: NaOMe / 0.33 h

4: 79 percent / n-BuLi, CuCN / diethyl ether / -70 - -50 °C

5: DIBAL-H / toluene / 3 h / -78 °C

6: toluene / 15 h / 23 °C

7: DMAP, Et₃N / pyridine / 26 h / 45 °C

8: DIBAL-H / toluene / 1 h / -78 °C

9: CBr₄, PPh₃ / CH₂Cl₂ / 1 h

10: Ph₃P / acetonitrile / 6 h

11: 14 percent / 1) n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1) -78 deg C, 1 h, 2) -78 to -50 deg C, 1.5 h

With dmap; n-butyllithium; carbon tetrabromide; dimethylsulfide borane complex; sodium methylate; diisobutylaluminium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; toluene; acetonitrile;
DOI:10.1016/S0040-4039(00)95219-5