Technology Process of (3S,5S,7S)-8-(tert-butyldiphenylsilyl)oxy-3,5-dihydroxy-4,4,7-trimethyloct-1-ene
There total 14 articles about (3S,5S,7S)-8-(tert-butyldiphenylsilyl)oxy-3,5-dihydroxy-4,4,7-trimethyloct-1-ene 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:
-
With
acetic acid; tetramethylammonium triacetoxyborohydride;
In
acetonitrile;
at -20 ℃;
for 48h;
DOI:10.1021/jo0503862
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C
1.2: 98 percent / tetrahydrofuran; hexane / 1 h / -50 °C
2.1: 96 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C
3.1: 93 percent / SmI2 / tetrahydrofuran; methanol / -78 - 20 °C
4.1: 99 percent / DDQ / CH2Cl2; H2O / 1.5 h / 0 - 20 °C
5.1: 69 percent / Me4NBH(OAc)3; AcOH / acetonitrile / 48 h / -20 °C
With
n-butyllithium; samarium diiodide; Dess-Martin periodane; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetramethylammonium triacetoxyborohydride;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; acetonitrile;
DOI:10.1021/jo0503862
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: 98 percent / oxalyl chloride DMSO; Et3N / CH2Cl2 / -78 - 20 °C
2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C
2.2: 98 percent / tetrahydrofuran; hexane / 1 h / -50 °C
3.1: 96 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C
4.1: 93 percent / SmI2 / tetrahydrofuran; methanol / -78 - 20 °C
5.1: 99 percent / DDQ / CH2Cl2; H2O / 1.5 h / 0 - 20 °C
6.1: 69 percent / Me4NBH(OAc)3; AcOH / acetonitrile / 48 h / -20 °C
With
n-butyllithium; samarium diiodide; oxalyl dichloride; Dess-Martin periodane; acetic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetramethylammonium triacetoxyborohydride;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; acetonitrile;
1.1: Swern oxidation;
DOI:10.1021/jo0503862
