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

Base Information

• Chemical Name: (2E,5R,6S,7E,9Z)-6-[(4-methoxyphenyl)methoxy]-5-methyl-12-(triphenylmethoxy)-2,7,9-dodecatrienal
• CAS No.: 773104-63-5
• Molecular Formula: C₄₀H₄₂O₄
• Molecular Weight: 586.771
• Mol file: 773104-63-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about (2E,5R,6S,7E,9Z)-6-[(4-methoxyphenyl)methoxy]-5-methyl-12-(triphenylmethoxy)-2,7,9-dodecatrienal 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: 66.0%

(2E,5R,6S,7E,9Z)-6-[(4-methoxyphenyl)methoxy]-5-methyl-12-(triphenylmethoxy)-2,7,9-dodecatrien-1-ol (773104-82-8) → (2E,5R,6S,7E,9Z)-6-[(4-methoxyphenyl)methoxy]-5-methyl-12-(triphenylmethoxy)-2,7,9-dodecatrienal (773104-63-5)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/ja048320w

Reference yield:

(2S,3R,5E)-3-methyl-5-heptene-1,2,7-triol (377751-08-1) → (2E,5R,6S,7E,9Z)-6-[(4-methoxyphenyl)methoxy]-5-methyl-12-(triphenylmethoxy)-2,7,9-dodecatrienal (773104-63-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 18.9 g / TsOH*H₂O / dimethylformamide / 17 h / 50 °C

2.1: 15.6 g / DIBAL-H / CH₂Cl₂; toluene / 4.5 h / -78 °C

3.1: 73 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / -78 - -20 °C

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

5.1: 12.2 g / PPh₃ / CH₂Cl₂ / 1 h / -78 °C

6.1: 93 percent / t-BuOK / 2-methyl-propan-2-ol / 15 h

7.1: Pd(PPh₃)4; Bu₃SnH / tetrahydrofuran / 1 h / 0 °C

7.2: 62 percent / I₂ / CH₂Cl₂ / 1 h / -78 - -25 °C

8.1: 96 percent / PdCl₂(MeCN)2; CuI / dimethylformamide / 20 h

9.1: 100 percent / Bu₄NF / tetrahydrofuran / 19 h / 0 °C

10.1: 66 percent / MnO₂ / CH₂Cl₂ / 1 h / 0 °C

With dmap; manganese(IV) oxide; dichloro bis(acetonitrile) palladium(II); copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium tert-butylate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 4.1: Dess-Martin oxidation / 5.1: Corey-Fuchs reaction / 8.1: Stille coupling;

DOI:10.1021/ja048320w

Reference yield:

ethyl (2E,5R,6S)-6,7-(isopropylidene)dioxy-5-methyl-2-heptenoate (377751-06-9) → (2E,5R,6S,7E,9Z)-6-[(4-methoxyphenyl)methoxy]-5-methyl-12-(triphenylmethoxy)-2,7,9-dodecatrienal (773104-63-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: DIBAL-H / CH₂Cl₂; toluene / 0.75 h / -78 °C

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

3.1: 18.9 g / TsOH*H₂O / dimethylformamide / 17 h / 50 °C

4.1: 15.6 g / DIBAL-H / CH₂Cl₂; toluene / 4.5 h / -78 °C

5.1: 73 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / -78 - -20 °C

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

7.1: 12.2 g / PPh₃ / CH₂Cl₂ / 1 h / -78 °C

8.1: 93 percent / t-BuOK / 2-methyl-propan-2-ol / 15 h

9.1: Pd(PPh₃)4; Bu₃SnH / tetrahydrofuran / 1 h / 0 °C

9.2: 62 percent / I₂ / CH₂Cl₂ / 1 h / -78 - -25 °C

10.1: 96 percent / PdCl₂(MeCN)2; CuI / dimethylformamide / 20 h

11.1: 100 percent / Bu₄NF / tetrahydrofuran / 19 h / 0 °C

12.1: 66 percent / MnO₂ / CH₂Cl₂ / 1 h / 0 °C

With dmap; manganese(IV) oxide; dichloro bis(acetonitrile) palladium(II); copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Amberlyst 15; potassium tert-butylate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 6.1: Dess-Martin oxidation / 7.1: Corey-Fuchs reaction / 10.1: Stille coupling;

DOI:10.1021/ja048320w

upstream raw materials:

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

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

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

ethyl (2E,5R,6S)-6,7-(isopropylidene)dioxy-5-methyl-2-heptenoate