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

Base Information

• Chemical Name: Benzoic acid (2Z,4E,10Z)-(1S,8S)-8-hydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,10-trienyl ester
• CAS No.: 122221-82-3
• Molecular Formula: C₂₈H₄₀O₅
• Molecular Weight: 456.623

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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

There total 12 articles about Benzoic acid (2Z,4E,10Z)-(1S,8S)-8-hydroxy-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: 90.0%

Benzoic acid (2Z,4E,10Z)-(1S,8S)-8-(tert-butyl-diphenyl-silanyloxy)-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,10-trienyl ester (122221-80-1) → Benzoic acid (2Z,4E,10Z)-(1S,8S)-8-hydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,10-trienyl ester (122221-82-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 12h;

DOI:10.1016/S0040-4039(00)95219-5

Reference yield:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → Benzoic acid (2Z,4E,10Z)-(1S,8S)-8-hydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,10-trienyl ester (122221-82-3)

Guidance literature:

Multi-step reaction with 11 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: 62 percent / 1) n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1) -78 deg C, 1 h, 2) -78 to -50 deg C, 1.5 h

11: 90 percent / n-Bu₄NF / tetrahydrofuran / 12 h

With dmap; n-butyllithium; carbon tetrabromide; tetrabutyl ammonium fluoride; 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:

(2S)-tetrahydro-5-oxofuran-2-carboxylic acid (21461-84-7) → Benzoic acid (2Z,4E,10Z)-(1S,8S)-8-hydroxy-1-(3-methoxycarbonyl-propyl)-hexadeca-2,4,10-trienyl ester (122221-82-3)

Guidance literature:

Multi-step reaction with 12 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: 62 percent / 1) n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1) -78 deg C, 1 h, 2) -78 to -50 deg C, 1.5 h

12: 90 percent / n-Bu₄NF / tetrahydrofuran / 12 h

With dmap; n-butyllithium; carbon tetrabromide; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; 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

upstream raw materials:

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

(2S)-tetrahydro-5-oxofuran-2-carboxylic acid

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

(Z)-5-(oct-2-en-1-yl)dihydrofuran-2(3H)-one.

Downstream raw materials:

C₃₅H₄₄O₆

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