Technology Process of (1S,3R,3aR,4S,7aS)-3-(3-acetoxy-4-methoxybenzyl)-7-methylene-1-vinyl-1,2,3,3a,7,7a-hexahydroinden-4-ol
There total 9 articles about (1S,3R,3aR,4S,7aS)-3-(3-acetoxy-4-methoxybenzyl)-7-methylene-1-vinyl-1,2,3,3a,7,7a-hexahydroinden-4-ol 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:
-
(1S,3R,3aR,4S,7aS)-3-(3-acetoxy-4-methoxybenzyl)-4-tert-butyldimethylsiloxy-7-methylene-1-vinyl-1,2,3,3a,7,7a-hexahydroindene;
With
tetrabutyl ammonium fluoride;
In
tetrahydrofuran;
at 20 ℃;
With
acetic anhydride;
In
tetrahydrofuran;
DOI:10.1055/s-2003-42114
- Guidance literature:
-
(1S,3R,3aR,4S,7aS)-3-(3-acetoxy-4-methoxybenzyl)-4-tert-butyldimethylsiloxy-7-methylene-1-vinyl-1,2,3,3a,7,7a-hexahydroindene;
With
tetrabutyl ammonium fluoride;
In
tetrahydrofuran;
at 20 ℃;
for 16h;
acetic anhydride;
In
tetrahydrofuran;
for 0.166667h;
Further stages.;
DOI:10.1002/chem.200700789
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: n-BuLi / tetrahydrofuran / -78 °C
1.2: 100 percent / tetrahydrofuran / -78 °C
2.1: 100 percent / DMAP; pyridine / 20 °C
3.1: 87 percent / Li; NH3 / tetrahydrofuran / -78 °C
4.1: 52 percent / DBU / toluene / 1.5 h / Heating
5.1: 90 percent / Dess-Martin periodinane / CH2Cl2 / 20 °C
6.1: 88 percent / t-BuOK / benzene
7.1: 76 percent / aq. TFA / tetrahydrofuran / 0 °C
8.1: 90 percent / aq. NaOH / propan-2-ol / 20 °C
9.1: 96 percent / DMAP / CH2Cl2 / 20 °C
10.1: 76 percent / (EtO)3P / Heating
11.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 °C
11.2: 92 percent / Ac2O / tetrahydrofuran
With
pyridine; dmap; sodium hydroxide; n-butyllithium; potassium tert-butylate; tetrabutyl ammonium fluoride; ammonia; lithium; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; triethyl phosphite;
In
tetrahydrofuran; dichloromethane; isopropyl alcohol; toluene; benzene;
5.1: Dess-Martin oxidation / 6.1: Wittig methylenation;
DOI:10.1055/s-2003-42114
