Technology Process of (1R,2R,3S,4S,5Z)-1-{3-(tert-butyldimethylsilanyloxy)-1-[3-(tert-butyldimethylsilanyloxy)propyl]-2,4-dimethylocta-5,7-dienyloxymethyl}-4-methoxybenzene
There total 16 articles about (1R,2R,3S,4S,5Z)-1-{3-(tert-butyldimethylsilanyloxy)-1-[3-(tert-butyldimethylsilanyloxy)propyl]-2,4-dimethylocta-5,7-dienyloxymethyl}-4-methoxybenzene 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:
-
(1-bromoallyl)trimethylsilane; (2R,3S,4R,5R)-3,8-bis(tert-butyldimethylsilanyloxy)-5-(4-methoxybenzyloxy)-2,4-dimethyloctanal;
With
chromium dichloride;
In
tetrahydrofuran;
at 20 ℃;
for 14h;
With
sodium hydride;
In
tetrahydrofuran;
at 0 - 20 ℃;
for 2.25h;
- Guidance literature:
-
With
sodium hydride;
In
tetrahydrofuran;
at 0 - 20 ℃;
for 2.25h;
DOI:10.1021/jm0204136
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: 95 percent / pyridinium sulfur trioxide
2.1: 95 percent / lithium borohydride / methanol; tetrahydrofuran / 2.33 h / 0 - 20 °C
3.1: 72 percent / pyridinium p-toluenesulfonate / benzene / 15 h / Heating
4.1: diisobutylaluminum hydride / tetrahydrofuran; CH2Cl2 / 1 h / 0 °C
5.1: pyridinium sulfur trioxide; diisopropylethylamine / dimethylsulfoxide; CH2Cl2 / 1 h / 20 °C
6.1: LDA / tetrahydrofuran / 1 h / -78 °C
6.2: 73 percent / tetrahydrofuran / 2 h / -78 - 20 °C
7.1: 2,6-lutidine / CH2Cl2 / 2 h / 20 °C
8.1: 997 mg / diisobutylaluminum hydride / tetrahydrofuran; CH2Cl2 / 1 h / 0 °C
9.1: pyridinium sulfur trioxide; diisopropylethylamine / dimethylsulfoxide; CH2Cl2 / 1 h / 20 °C
10.1: CrCl2 / tetrahydrofuran / 14 h / 20 °C
11.1: 622 mg / NaH / tetrahydrofuran / 2.25 h / 0 - 20 °C
With
2,6-dimethylpyridine; chromium dichloride; lithium borohydride; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; benzene;
2.1: Evans syn-aldol condensation / 7.2: Heathcock's aldol reaction / 11.1: Nozaki-Hiyama reaction;
DOI:10.1021/jm0204136
