(2E,6E,8E)-(4R,5S,10S,11R,12S)-11-(4-Methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-5-triethylsilanyloxy-tetradeca-2,6,8-trienoic acid ethyl ester

Base Information

• Chemical Name: (2E,6E,8E)-(4R,5S,10S,11R,12S)-11-(4-Methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-5-triethylsilanyloxy-tetradeca-2,6,8-trienoic acid ethyl ester
• CAS No.: 637742-13-3
• Molecular Formula: C₃₆H₆₀O₅Si
• Molecular Weight: 600.955

Synonyms:

Chemical Property of (2E,6E,8E)-(4R,5S,10S,11R,12S)-11-(4-Methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-5-triethylsilanyloxy-tetradeca-2,6,8-trienoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,6E,8E)-(4R,5S,10S,11R,12S)-11-(4-Methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-5-triethylsilanyloxy-tetradeca-2,6,8-trienoic acid ethyl ester

There total 11 articles about (2E,6E,8E)-(4R,5S,10S,11R,12S)-11-(4-Methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-5-triethylsilanyloxy-tetradeca-2,6,8-trienoic acid ethyl 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:

(4R,5S)-4-(S)-sec-butyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane (637742-08-6) → (2E,6E,8E)-(4R,5S,10S,11R,12S)-11-(4-Methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-5-triethylsilanyloxy-tetradeca-2,6,8-trienoic acid ethyl ester (637742-13-3)

Guidance literature:

Multi-step reaction with 12 steps

1: 91 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 12 h / 0 °C

2: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

3: 3.5 g / tetrahydrofuran / 12 h / Heating

4: 93 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 0 °C

5: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

6: tetrahydrofuran / Heating

7: diisobutylaluminum hydride / CH₂Cl₂; hexane / 0 °C

8: tetrapropylammonium perruthenate; N-methyl morpholine N-oxide / CH₂Cl₂ / 20 °C

9: 75 percent / tin(II) trifluoromethanesulfonate; (S)-1-methyl-2-[(N-1-naphthylamino)-methyl]pyrrolidine; dibutyltin diacetate / CH₂Cl₂ / 16 h / -78 °C

10: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

11: diisobutylaluminum hydride / CH₂Cl₂; hexane / -78 °C

12: tetrahydrofuran / Heating

With 2,6-dimethylpyridine; tin(II) trifluoromethanesulfonate; tetrapropylammonium perruthennate; dibutyltin diacetate; oxalyl dichloride; diisobutylaluminium hydride; (2S)-1-methyl-2-<(N-1-naphthylamino)methyl>pyrrolidine; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 2: Swern oxidation / 3: Wittig reaction / 5: Swern oxidation / 6: Wittig reaction / 12: Wittig reaction;

DOI:10.1039/b305818b

Reference yield:

(2R,3R,4S)-3-(4-Methoxy-benzyloxy)-2,4-dimethyl-hexanal → (2E,6E,8E)-(4R,5S,10S,11R,12S)-11-(4-Methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-5-triethylsilanyloxy-tetradeca-2,6,8-trienoic acid ethyl ester (637742-13-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 3.5 g / tetrahydrofuran / 12 h / Heating

2: 93 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 0 °C

3: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

4: tetrahydrofuran / Heating

5: diisobutylaluminum hydride / CH₂Cl₂; hexane / 0 °C

6: tetrapropylammonium perruthenate; N-methyl morpholine N-oxide / CH₂Cl₂ / 20 °C

7: 75 percent / tin(II) trifluoromethanesulfonate; (S)-1-methyl-2-[(N-1-naphthylamino)-methyl]pyrrolidine; dibutyltin diacetate / CH₂Cl₂ / 16 h / -78 °C

8: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

9: diisobutylaluminum hydride / CH₂Cl₂; hexane / -78 °C

10: tetrahydrofuran / Heating

With 2,6-dimethylpyridine; tin(II) trifluoromethanesulfonate; tetrapropylammonium perruthennate; dibutyltin diacetate; oxalyl dichloride; diisobutylaluminium hydride; (2S)-1-methyl-2-<(N-1-naphthylamino)methyl>pyrrolidine; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1: Wittig reaction / 3: Swern oxidation / 4: Wittig reaction / 10: Wittig reaction;

DOI:10.1039/b305818b

Reference yield:

(2S,3R,4S)-3-(4-Methoxy-benzyloxy)-2,4-dimethyl-hexan-1-ol (637741-20-9) → (2E,6E,8E)-(4R,5S,10S,11R,12S)-11-(4-Methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-5-triethylsilanyloxy-tetradeca-2,6,8-trienoic acid ethyl ester (637742-13-3)

Guidance literature:

Multi-step reaction with 11 steps

1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

2: 3.5 g / tetrahydrofuran / 12 h / Heating

3: 93 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 0 °C

4: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

5: tetrahydrofuran / Heating

6: diisobutylaluminum hydride / CH₂Cl₂; hexane / 0 °C

7: tetrapropylammonium perruthenate; N-methyl morpholine N-oxide / CH₂Cl₂ / 20 °C

8: 75 percent / tin(II) trifluoromethanesulfonate; (S)-1-methyl-2-[(N-1-naphthylamino)-methyl]pyrrolidine; dibutyltin diacetate / CH₂Cl₂ / 16 h / -78 °C

9: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

10: diisobutylaluminum hydride / CH₂Cl₂; hexane / -78 °C

11: tetrahydrofuran / Heating

With 2,6-dimethylpyridine; tin(II) trifluoromethanesulfonate; tetrapropylammonium perruthennate; dibutyltin diacetate; oxalyl dichloride; diisobutylaluminium hydride; (2S)-1-methyl-2-<(N-1-naphthylamino)methyl>pyrrolidine; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1: Swern oxidation / 2: Wittig reaction / 4: Swern oxidation / 5: Wittig reaction / 11: Wittig reaction;

DOI:10.1039/b305818b

upstream raw materials:

(carbethoxyethylidene)triphenylphosphorane

(4E,6E)-(2S,3S,8S,9R,10S)-9-(4-Methoxy-benzyloxy)-2,4,6,8,10-pentamethyl-3-triethylsilanyloxy-dodeca-4,6-dienal

(4R,5S)-4-(S)-sec-butyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane

(2S,3R,4S)-3-(4-Methoxy-benzyloxy)-2,4-dimethyl-hexan-1-ol

Downstream raw materials:

(2E,6E,8E)-(4R,10S,11R,12S)-11-(4-Methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-5-oxo-tetradeca-2,6,8-trienoic acid (1R,2R,3S)-3-carboxy-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-propyl ester

(1R,2S,3R)-1-[(4-methoxybenzyloxy)methyl]-2,3-bis(4-methoxybenzyloxy)-4-hydroxybutyl (2E,4R,5S,6E,8E,10S,11R,12S)-2,4,6,8,10,12-hexamethyl-5-hydroxy-11-(4-methoxybenzyloxy)-2,6,8-tetradecatrienoate

(2E,6E,8E)-(4R,5S,10S,11R,12S)-11-(4-Methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-5-triethylsilanyloxy-tetradeca-2,6,8-trienoic acid

(2E,4R,5S,6E,8E,10S,11R,12S)-2,4,6,8,10,12-hexamethyl-5-(triethylsiloxy)-11-(4-methoxybenzyloxy)-2,6,8-tetradecatrienal

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