Technology Process of (E)-(4S,5R,6S)-5-(4-Methoxy-benzyloxy)-2,4,6-trimethyl-hexadec-2-en-1-ol
There total 14 articles about (E)-(4S,5R,6S)-5-(4-Methoxy-benzyloxy)-2,4,6-trimethyl-hexadec-2-en-1-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
diisobutylaluminium hydride;
In
hexane; dichloromethane;
at -78 ℃;
DOI:10.1021/ja0057272
- Guidance literature:
-
Multi-step reaction with 12 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
With
pyridine; lithium aluminium tetrahydride; lithium borohydride; tin(II) trifluoromethanesulfonate; 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;
DOI:10.1021/ja0057272
- Guidance literature:
-
Multi-step reaction with 5 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
With
oxalyl dichloride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; hexane; dichloromethane;
3: Swern oxidation / 4: Wittig olefination;
DOI:10.1021/ja0057272
