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
There total 14 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 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:
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637741-24-3
(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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637742-15-5
(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
- Guidance literature:
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With
sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene;
In
water; tert-butyl alcohol;
at 20 ℃;
for 20h;
DOI:10.1039/b305818b
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637742-15-5
(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
- Guidance literature:
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Multi-step reaction with 15 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
With
2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; tin(II) trifluoromethanesulfonate; tetrapropylammonium perruthennate; dibutyltin diacetate; 2-methyl-but-2-ene; oxalyl dichloride; diisobutylaluminium hydride; (2S)-1-methyl-2-<(N-1-naphthylamino)methyl>pyrrolidine; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine;
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
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637742-15-5
(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
- Guidance literature:
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Multi-step reaction with 13 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
With
2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; tin(II) trifluoromethanesulfonate; tetrapropylammonium perruthennate; dibutyltin diacetate; 2-methyl-but-2-ene; oxalyl dichloride; diisobutylaluminium hydride; (2S)-1-methyl-2-<(N-1-naphthylamino)methyl>pyrrolidine; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine;
In
tetrahydrofuran; hexane; dichloromethane; water; tert-butyl alcohol;
1: Wittig reaction / 3: Swern oxidation / 4: Wittig reaction / 10: Wittig reaction;
DOI:10.1039/b305818b