Technology Process of (2E,4E)-(6S,7R,8S)-7-(4-Methoxy-benzyloxy)-2,4,6,8-tetramethyl-octadeca-2,4-dienoic acid ethyl ester
There total 16 articles about (2E,4E)-(6S,7R,8S)-7-(4-Methoxy-benzyloxy)-2,4,6,8-tetramethyl-octadeca-2,4-dienoic 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:
- Guidance literature:
-
Multi-step reaction with 14 steps
1: 83 percent / Sn(OTf)2; SnO; (S)-1-methyl-2-[(N-1-naphthylamino)-methyl]pyrrolidine / CH2Cl2 / 5 h / -78 °C
2: pyridine / 1,2-dichloro-ethane / 0.17 h / Heating
3: Bu3SnH; AIBN / toluene / 0.17 h / 110 °C
4: 5.17 g / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C
5: 91 percent / (COCl)2; DMSO; triethylamine / CH2Cl2 / -78 - 20 °C
6: Sn(OTf)2; Bu2Sn(OAc)2; (S)-1-methyl-2-[(N-naphthylamino)-methyl]pyrrolidine / CH2Cl2 / -78 °C
7: LiBH4 / tetrahydrofuran / -5 °C
8: 95 percent / TsOH / CH2Cl2 / 20 °C
9: 96 percent / DIBAL / CH2Cl2; hexane / 20 °C
10: 92 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C
11: tetrahydrofuran / Heating
12: 98 percent / DIBAL / CH2Cl2; hexane / -78 °C
13: 88 percent / TPAP; NMO / CH2Cl2 / 20 °C
14: 87 percent / tetrahydrofuran / Heating
With
pyridine; lithium aluminium tetrahydride; lithium borohydride; tin(II) trifluoromethanesulfonate; N-methyl-2-indolinone; tetrapropylammonium perruthennate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; tin(II) oxide; diisobutylaluminium hydride; dibutyltin diacetate; (2S)-1-methyl-2-<(N-1-naphthylamino)methyl>pyrrolidine; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; hexane; dichloromethane; 1,2-dichloro-ethane; toluene;
5: Swern oxidation / 10: Swern oxidation / 11: Wittig olefination / 14: Wittig olefination;
DOI:10.1021/ja0057272
- Guidance literature:
-
Multi-step reaction with 7 steps
1: 95 percent / TsOH / CH2Cl2 / 20 °C
2: 96 percent / DIBAL / CH2Cl2; hexane / 20 °C
3: 92 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C
4: tetrahydrofuran / Heating
5: 98 percent / DIBAL / CH2Cl2; hexane / -78 °C
6: 88 percent / TPAP; NMO / CH2Cl2 / 20 °C
7: 87 percent / tetrahydrofuran / Heating
With
N-methyl-2-indolinone; tetrapropylammonium perruthennate; oxalyl dichloride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; hexane; dichloromethane;
3: Swern oxidation / 4: Wittig olefination / 7: Wittig olefination;
DOI:10.1021/ja0057272
