Technology Process of (6S,8S)-8-(4-methoxybenzyloxy)-7,7-dimethylundeca-3,9-dien-1-yn-6-ol
There total 13 articles about (6S,8S)-8-(4-methoxybenzyloxy)-7,7-dimethylundeca-3,9-dien-1-yn-6-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
tetrabutyl ammonium fluoride;
In
tetrahydrofuran;
at 20 ℃;
for 14h;
DOI:10.1021/ja0443068
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: (COCl)2; DMSO; Et3N / CH2Cl2 / 2.5 h / -78 °C
2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 - 0 °C
2.2: 2.315 g / tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C
3.1: 83 percent / Red-Al / tetrahydrofuran; toluene / 25 h / Heating
4.1: Et3N; KHMDS / tetrahydrofuran / 3 h / -78 - 20 °C
5.1: 2.20 g / aq. AcOH / tetrahydrofuran / 12 h / 60 °C
6.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
7.1: 152.0 mg / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 0.92 h / -78 °C
8.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 0 °C
8.2: tetrahydrofuran; hexane / 0.5 h / -78 °C
9.1: 96.8 mg / chloroacetic acid / methanol; CH2Cl2 / 14 h / 20 °C
10.1: 94 percent / TBAF / tetrahydrofuran / 14 h / 20 °C
With
2,6-dimethylpyridine; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; acetic acid; dimethyl sulfoxide; triethylamine; chloroacetic acid; sodium bis(2-methoxyethoxy)aluminium dihydride;
In
tetrahydrofuran; methanol; hexane; dichloromethane; toluene;
1.1: Swern oxidation / 7.1: Swern oxidation / 8.1: Peterson olefination;
DOI:10.1021/ja0443068
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 - 0 °C
1.2: 2.315 g / tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C
2.1: 83 percent / Red-Al / tetrahydrofuran; toluene / 25 h / Heating
3.1: Et3N; KHMDS / tetrahydrofuran / 3 h / -78 - 20 °C
4.1: 2.20 g / aq. AcOH / tetrahydrofuran / 12 h / 60 °C
5.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
6.1: 152.0 mg / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 0.92 h / -78 °C
7.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 0 °C
7.2: tetrahydrofuran; hexane / 0.5 h / -78 °C
8.1: 96.8 mg / chloroacetic acid / methanol; CH2Cl2 / 14 h / 20 °C
9.1: 94 percent / TBAF / tetrahydrofuran / 14 h / 20 °C
With
2,6-dimethylpyridine; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; acetic acid; dimethyl sulfoxide; triethylamine; chloroacetic acid; sodium bis(2-methoxyethoxy)aluminium dihydride;
In
tetrahydrofuran; methanol; hexane; dichloromethane; toluene;
6.1: Swern oxidation / 7.1: Peterson olefination;
DOI:10.1021/ja0443068
