Technology Process of (1S,2R,5S,6R,9R,10R,13S,14S)-12-(hydroxymethyl)-2,6-dimethyl-9-propan-2-yltricyclo[8.4.0.05,14]tetradec-11-ene-1,13-diol
There total 18 articles about (1S,2R,5S,6R,9R,10R,13S,14S)-12-(hydroxymethyl)-2,6-dimethyl-9-propan-2-yltricyclo[8.4.0.05,14]tetradec-11-ene-1,13-diol 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:
-
C20H34O2;
With
oxygen; triphenylphosphine;
In
[D3]acetonitrile;
at 25 ℃;
for 12h;
under 760.051 Torr;
UV-irradiation;
With
trimethylphosphane;
In
toluene;
at 0 ℃;
for 0.5h;
- Guidance literature:
-
C21H36O4;
With
pyridine; Burgess Reagent;
at 0 - 20 ℃;
for 8h;
With
diisobutylaluminium hydride;
In
hexane; dichloromethane;
at -78 ℃;
for 3h;
Further stages;
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: dmap / dichloromethane / 2.17 h / 0 - 20 °C
2.1: sodium hydrogencarbonate / acetonitrile / 15 h / 160 °C / Sealed tube
3.1: Wilkinson's catalyst; hydrogen / toluene / 25 °C / 51716.2 Torr / Autoclave
4.1: borane-THF / tetrahydrofuran / 4.5 h / 80 °C
4.2: 12.2 h / 0 - 25 °C
5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / water; dimethyl sulfoxide / 2 h / 80 °C
6.1: sodium hydrogencarbonate / dimethyl sulfoxide / 5 h / 25 °C
7.1: samarium diiodide / tetrahydrofuran; water / 0.5 h / 0 °C / Inert atmosphere
8.1: lithium hexamethyldisilazane / tetrahydrofuran; diethyl ether / 1.5 h / -78 - -40 °C
8.2: 1.5 h / -78 - -40 °C
8.3: 1 h / 25 °C
9.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 - -40 °C
9.2: 2.17 h / -78 - 0 °C
10.1: 5,15,10,20-tetraphenylporphyrin; sodium hydrogencarbonate; oxygen / acetonitrile / 16 h / 20 °C / Irradiation
10.2: 1 h / 20 °C
With
dmap; Wilkinson's catalyst; samarium diiodide; borane-THF; hydrogen; oxygen; 5,15,10,20-tetraphenylporphyrin; sodium hydrogencarbonate; lithium hexamethyldisilazane; lithium diisopropyl amide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; dimethyl sulfoxide; toluene; acetonitrile;
DOI:10.1021/jacs.9b08983
