(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

Base Information

• Chemical Name: (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
• CAS No.: 637742-17-7
• Molecular Formula: C₅₇H₇₂O₁₃
• Molecular Weight: 965.191

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 18 articles about (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 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:

(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)-2,3-bis-(4-methoxy-benzyloxy)-1-(4-methoxy-benzyloxymethyl)-4-oxo-butyl ester → (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 (637742-17-7)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; at 20 ℃;

DOI:10.1039/b305818b

Reference yield:

(4R,5S)-4-(S)-sec-butyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane (637742-08-6) → (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 (637742-17-7)

Guidance literature:

Multi-step reaction with 19 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

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

14: 362 mg / tetrapropylammonium perruthenate; N-methyl morpholine N-oxide / CH₂Cl₂ / 1 h / 20 °C

15: 89 percent / sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 20 h / 20 °C

16: dicyclohexyl carbodiimide; N,N-dimethylaminopyridine; N,N-dimethylaminopyridine hydrochloride / CH₂Cl₂ / 12 h / Heating

17: aq. HCl / tetrahydrofuran / 20 °C

18: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 20 °C

19: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 20 °C

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; dmap; sodium chlorite; sodium dihydrogenphosphate; tin(II) trifluoromethanesulfonate; tetrapropylammonium perruthennate; dibutyltin diacetate; 2-methyl-but-2-ene; oxalyl dichloride; 4-(dimethylamino)pyridine hydrochloride; diisobutylaluminium hydride; (2S)-1-methyl-2-<(N-1-naphthylamino)methyl>pyrrolidine; Dess-Martin periodane; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; hexane; dichloromethane; water; tert-butyl alcohol; 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,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 (637742-17-7)

Guidance literature:

Multi-step reaction with 17 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

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

12: 362 mg / tetrapropylammonium perruthenate; N-methyl morpholine N-oxide / CH₂Cl₂ / 1 h / 20 °C

13: 89 percent / sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 20 h / 20 °C

14: dicyclohexyl carbodiimide; N,N-dimethylaminopyridine; N,N-dimethylaminopyridine hydrochloride / CH₂Cl₂ / 12 h / Heating

15: aq. HCl / tetrahydrofuran / 20 °C

16: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 20 °C

17: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 20 °C

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; dmap; sodium chlorite; sodium dihydrogenphosphate; tin(II) trifluoromethanesulfonate; tetrapropylammonium perruthennate; dibutyltin diacetate; 2-methyl-but-2-ene; oxalyl dichloride; 4-(dimethylamino)pyridine hydrochloride; diisobutylaluminium hydride; (2S)-1-methyl-2-<(N-1-naphthylamino)methyl>pyrrolidine; Dess-Martin periodane; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; hexane; dichloromethane; water; tert-butyl alcohol; 1: Wittig reaction / 3: Swern oxidation / 4: Wittig reaction / 10: Wittig reaction;

DOI:10.1039/b305818b

upstream raw materials:

(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

(E)-(4S,5R,6S)-5-(4-Methoxy-benzyloxy)-2,4,6-trimethyl-oct-2-en-1-ol

ethyl (2E,4S,5R,6S)-2,4,6-trimethyl-5-(4-methoxybenzyloxy)-2-octenoate

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