(2E,4E,8E,10E,14E)-(12R,13R,16S)-13-Hydroxy-2,10,12,14,16-pentamethyl-18-phenyl-octadeca-2,4,8,10,14-pentaen-6-ynoic acid

Base Information

• Chemical Name: (2E,4E,8E,10E,14E)-(12R,13R,16S)-13-Hydroxy-2,10,12,14,16-pentamethyl-18-phenyl-octadeca-2,4,8,10,14-pentaen-6-ynoic acid
• CAS No.: 770711-62-1
• Molecular Formula: C₂₉H₃₆O₃
• Molecular Weight: 432.603
• Mol file: 770711-62-1.mol

Synonyms:(2E,4E,8E,10E,14E)-(12R,13R,16S)-13-Hydroxy-2,10,12,14,16-pentamethyl-18-phenyl-octadeca-2,4,8,10,14-pentaen-6-ynoic acid

Chemical Property of (2E,4E,8E,10E,14E)-(12R,13R,16S)-13-Hydroxy-2,10,12,14,16-pentamethyl-18-phenyl-octadeca-2,4,8,10,14-pentaen-6-ynoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,4E,8E,10E,14E)-(12R,13R,16S)-13-Hydroxy-2,10,12,14,16-pentamethyl-18-phenyl-octadeca-2,4,8,10,14-pentaen-6-ynoic acid

There total 15 articles about (2E,4E,8E,10E,14E)-(12R,13R,16S)-13-Hydroxy-2,10,12,14,16-pentamethyl-18-phenyl-octadeca-2,4,8,10,14-pentaen-6-ynoic 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: 96.0%

ethyl (2E,4E,8E,10E,12R,13R,14E,16S)-2,10,12,14,16-pentamethyl-13-hydroxy-18-phenyl-2,4,8,10,14-octadecapentaen-6-ynoate (770711-61-0) → (2E,4E,8E,10E,14E)-(12R,13R,16S)-13-Hydroxy-2,10,12,14,16-pentamethyl-18-phenyl-octadeca-2,4,8,10,14-pentaen-6-ynoic acid (770711-62-1)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; water; at 23 ℃; for 6h;

DOI:10.1021/ol048905v

Reference yield:

(S)-4-methyl-6-phenyl-2-hexyne (770711-55-2) → (2E,4E,8E,10E,14E)-(12R,13R,16S)-13-Hydroxy-2,10,12,14,16-pentamethyl-18-phenyl-octadeca-2,4,8,10,14-pentaen-6-ynoic acid (770711-62-1)

Guidance literature:

Multi-step reaction with 13 steps

1.1: Cp₂Zr(H)Cl / tetrahydrofuran / 2 h / 60 °C

1.2: 87 percent / 3 h / 45 °C

2.1: tBuOK; nBuLi; (+)-Ipc₂BOMe / tetrahydrofuran; hexane; diethyl ether / 15 h / -78 °C

2.2: 80 percent / NaOAc; H₂O₂ / H₂O; tetrahydrofuran; diethyl ether / 15 h / 23 °C

3.1: 95 percent / imidazole; DMAP / dimethylformamide / 12 h / 23 °C

4.1: 4.18 g / AD-mix-α / 2-methyl-propan-2-ol; H2O / 48 h / 23 °C

5.1: 3.75 g / NaIO₄ / tetrahydrofuran; H₂O / 0.5 h / 23 °C

6.1: Ph₃P; Zn / CH₂Cl₂ / 6 h / 23 °C

7.1: nBuLi; ZnBr₂ / tetrahydrofuran; hexane / 0.92 h / -78 - -23 °C

7.2: 75 percent / DIBAH / tetrahydrofuran; hexane / 12 h / 23 °C

8.1: 100 percent / Pd(tBu₃P)2 / tetrahydrofuran; toluene / 1 h / 23 °C

9.1: 98 percent / K₂CO₃ / methanol / 3 h / 23 °C

10.1: HZrCp₂Cl / tetrahydrofuran / 4 h / 23 °C

10.2: 86 percent / I₂ / 2 h / 0 - 23 °C

11.1: iPr₂NH; nBuLi; ZnBr₂ / tetrahydrofuran; hexane / 0.58 h / -78 - 0 °C

11.2: 94 percent / Cl₂Pd(PPh₃)2; DIBAL-H / tetrahydrofuran; hexane / 3 h / 23 °C

12.1: 85 percent / TBAF / tetrahydrofuran / 24 h / 23 °C

13.1: 96 percent / LiOH / tetrahydrofuran; methanol; H₂O / 6 h / 23 °C

With 1H-imidazole; dmap; lithium hydroxide; sodium periodate; AD-mix-α; Schwartz's reagent; n-butyllithium; bis(tri-t-butylphosphine)palladium⁽⁰⁾; potassium tert-butylate; tetrabutyl ammonium fluoride; potassium carbonate; diisopropylamine; triphenylphosphine; (+)-B-methoxydiisocamphenylborane; zinc dibromide; zinc; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 2.1: Brown's asymmetric crotylboration;

DOI:10.1021/ol048905v

Reference yield:

(S)-1,1-dibromo-3-methyl-5-phenyl-1-pentene (770711-54-1) → (2E,4E,8E,10E,14E)-(12R,13R,16S)-13-Hydroxy-2,10,12,14,16-pentamethyl-18-phenyl-octadeca-2,4,8,10,14-pentaen-6-ynoic acid (770711-62-1)

Guidance literature:

Multi-step reaction with 14 steps

1.1: nBuLi / tetrahydrofuran; hexane / 12 h / -78 - 23 °C

2.1: Cp₂Zr(H)Cl / tetrahydrofuran / 2 h / 60 °C

2.2: 87 percent / 3 h / 45 °C

3.1: tBuOK; nBuLi; (+)-Ipc₂BOMe / tetrahydrofuran; hexane; diethyl ether / 15 h / -78 °C

3.2: 80 percent / NaOAc; H₂O₂ / H₂O; tetrahydrofuran; diethyl ether / 15 h / 23 °C

4.1: 95 percent / imidazole; DMAP / dimethylformamide / 12 h / 23 °C

5.1: 4.18 g / AD-mix-α / 2-methyl-propan-2-ol; H2O / 48 h / 23 °C

6.1: 3.75 g / NaIO₄ / tetrahydrofuran; H₂O / 0.5 h / 23 °C

7.1: Ph₃P; Zn / CH₂Cl₂ / 6 h / 23 °C

8.1: nBuLi; ZnBr₂ / tetrahydrofuran; hexane / 0.92 h / -78 - -23 °C

8.2: 75 percent / DIBAH / tetrahydrofuran; hexane / 12 h / 23 °C

9.1: 100 percent / Pd(tBu₃P)2 / tetrahydrofuran; toluene / 1 h / 23 °C

10.1: 98 percent / K₂CO₃ / methanol / 3 h / 23 °C

11.1: HZrCp₂Cl / tetrahydrofuran / 4 h / 23 °C

11.2: 86 percent / I₂ / 2 h / 0 - 23 °C

12.1: iPr₂NH; nBuLi; ZnBr₂ / tetrahydrofuran; hexane / 0.58 h / -78 - 0 °C

12.2: 94 percent / Cl₂Pd(PPh₃)2; DIBAL-H / tetrahydrofuran; hexane / 3 h / 23 °C

13.1: 85 percent / TBAF / tetrahydrofuran / 24 h / 23 °C

14.1: 96 percent / LiOH / tetrahydrofuran; methanol; H₂O / 6 h / 23 °C

With 1H-imidazole; dmap; lithium hydroxide; sodium periodate; AD-mix-α; Schwartz's reagent; n-butyllithium; bis(tri-t-butylphosphine)palladium⁽⁰⁾; potassium tert-butylate; tetrabutyl ammonium fluoride; potassium carbonate; diisopropylamine; triphenylphosphine; (+)-B-methoxydiisocamphenylborane; zinc dibromide; zinc; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 3.1: Brown's asymmetric crotylboration;

DOI:10.1021/ol048905v

upstream raw materials:

ethyl (2E,4E,8E,10E,12R,13R,14E,16S)-2,10,12,14,16-pentamethyl-13-hydroxy-18-phenyl-2,4,8,10,14-octadecapentaen-6-ynoate

(S)-4-methyl-6-phenyl-2-hexyne

(S)-1,1-dibromo-3-methyl-5-phenyl-1-pentene

(4R,5R,6E,8S)-4,6,8-trimethyl-5-(t-butyldimethylsilyloxy)-10-phenyl-6-decen-2-yne