(2E,5R,6S,7Z,9E)-6-[(4-methoxyphenyl)methoxy]-5-methyl-12-(triphenylmethoxy)-2,7,9-dodecatrien-1-ol

Base Information

• Chemical Name: (2E,5R,6S,7Z,9E)-6-[(4-methoxyphenyl)methoxy]-5-methyl-12-(triphenylmethoxy)-2,7,9-dodecatrien-1-ol
• CAS No.: 377751-14-9
• Molecular Formula: C₄₀H₄₄O₄
• Molecular Weight: 588.787
• Mol file: 377751-14-9.mol

Synonyms:(2E,5R,6S,7Z,9E)-6-[(4-methoxyphenyl)methoxy]-5-methyl-12-(triphenylmethoxy)-2,7,9-dodecatrien-1-ol

Chemical Property of (2E,5R,6S,7Z,9E)-6-[(4-methoxyphenyl)methoxy]-5-methyl-12-(triphenylmethoxy)-2,7,9-dodecatrien-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,5R,6S,7Z,9E)-6-[(4-methoxyphenyl)methoxy]-5-methyl-12-(triphenylmethoxy)-2,7,9-dodecatrien-1-ol

There total 27 articles about (2E,5R,6S,7Z,9E)-6-[(4-methoxyphenyl)methoxy]-5-methyl-12-(triphenylmethoxy)-2,7,9-dodecatrien-1-ol 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: 100.0%

(2E,5R,6S,7Z,9E)-1-(tert-butyldiphenylsilyloxy)-6-[(4-methoxyphenyl)methoxy]-5-methyl-12-(triphenylmethoxy)-2,7,9-dodecatriene (377751-12-7) → (2E,5R,6S,7Z,9E)-6-[(4-methoxyphenyl)methoxy]-5-methyl-12-(triphenylmethoxy)-2,7,9-dodecatrien-1-ol (377751-14-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 2.5h;

DOI:10.1021/ja048320w

Reference yield:

(2S,3R,5E)-3-methyl-5-heptene-1,2,7-triol (377751-08-1) → (2E,5R,6S,7Z,9E)-6-[(4-methoxyphenyl)methoxy]-5-methyl-12-(triphenylmethoxy)-2,7,9-dodecatrien-1-ol (377751-14-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 18.9 g / TsOH*H₂O / dimethylformamide / 17 h / 50 °C

2: 15.6 g / DIBAL-H / CH₂Cl₂; toluene / 4.5 h / -78 °C

3: 73 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / -78 - -20 °C

4: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 °C

5: 12.2 g / PPh₃ / CH₂Cl₂ / 1 h / -78 °C

6: 80 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

7: 91 percent / Et₃N; Pd(PPh₃)4; CuI / 2.5 h

8: 66 percent / H₂; quinoline; 1-hexene / Lindlar catalyst / 2 h / atmospheric pressure

9: 100 percent / Bu₄NF / tetrahydrofuran / 2.5 h / 0 °C

With quinoline; dmap; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; 1-hexene; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 4: Dess-Martin oxidation / 5: Corey-Fuchs reaction;

DOI:10.1021/ja048320w

Reference yield:

(2E,5R,6S)-6,7-(isopropylidene)dioxy-5-methyl-2-hepten-1-ol (377751-07-0) → (2E,5R,6S,7Z,9E)-6-[(4-methoxyphenyl)methoxy]-5-methyl-12-(triphenylmethoxy)-2,7,9-dodecatrien-1-ol (377751-14-9)

Guidance literature:

Multi-step reaction with 10 steps

1: Amberlyst 15 / aq. methanol / 12 h / 50 °C

2: 18.9 g / TsOH*H₂O / dimethylformamide / 17 h / 50 °C

3: 15.6 g / DIBAL-H / CH₂Cl₂; toluene / 4.5 h / -78 °C

4: 73 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / -78 - -20 °C

5: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 °C

6: 12.2 g / PPh₃ / CH₂Cl₂ / 1 h / -78 °C

7: 80 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

8: 91 percent / Et₃N; Pd(PPh₃)4; CuI / 2.5 h

9: 66 percent / H₂; quinoline; 1-hexene / Lindlar catalyst / 2 h / atmospheric pressure

10: 100 percent / Bu₄NF / tetrahydrofuran / 2.5 h / 0 °C

With quinoline; dmap; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; 1-hexene; Amberlyst 15; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 5: Dess-Martin oxidation / 6: Corey-Fuchs reaction;

DOI:10.1021/ja048320w

upstream raw materials:

(2E,5R,6S,7Z,9E)-1-(tert-butyldiphenylsilyloxy)-6-[(4-methoxyphenyl)methoxy]-5-methyl-12-(triphenylmethoxy)-2,7,9-dodecatriene

trityl chloride

(2S,3R,5E)-3-methyl-5-heptene-1,2,7-triol

(2E,5R,6S)-6,7-(isopropylidene)dioxy-5-methyl-2-hepten-1-ol

Downstream raw materials:

(1S,2S,3S,4Z,6S,7S,8R)-2-formyl-7-[(4-methoxyphenyl)methoxy]-8-methyl-3-[2-(triphenylmethoxy)ethyl]bicyclo[4.3.0]non-4-ene

(2E,5R,6S,7Z,9E)-6-[(4-methoxyphenyl)methoxy]-5-methyl-12-(triphenylmethoxy)-2,7,9-dodecatrien-1-al