Technology Process of (2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-2-methylpentan-1-one
There total 8 articles about (2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-2-methylpentan-1-one 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:
-
(S)-3-propanoyl-4-benzyl-1,3-thiazolidine-2-thione;
With
titanium tetrachloride;
In
dichloromethane;
at 0 ℃;
for 0.333333h;
Inert atmosphere;
With
(-)-sparteine;
In
dichloromethane;
at -78 - 0 ℃;
for 0.383333h;
Inert atmosphere;
propionaldehyde;
In
dichloromethane;
at -78 - 0 ℃;
diastereoselective reaction;
Inert atmosphere;
DOI:10.15227/orgsyn.088.0364
- Guidance literature:
-
(S)-3-propanoyl-4-benzyl-1,3-thiazolidine-2-thione;
With
titanium tetrachloride;
In
dichloromethane;
at 0 ℃;
for 1h;
With
N-ethyl-N,N-diisopropylamine;
In
dichloromethane;
at 0 ℃;
for 0.75h;
propionaldehyde;
In
dichloromethane;
at -94 ℃;
for 6.5h;
Temperature;
Overall yield = 88 percent; Overall yield = 250 g;
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: triethylamine / dichloromethane / Inert atmosphere; Reflux
1.2: 1 h / Inert atmosphere; Reflux
2.1: carbon disulfide; potassium hydroxide / water / 16 h / 100 °C / Inert atmosphere; Reflux
3.1: triethylamine; dmap / dichloromethane / 3 h / 20 °C / Inert atmosphere
4.1: titanium tetrachloride / dichloromethane / 0.08 h / 0 °C / Inert atmosphere
4.2: 0.25 h / -78 - 0 °C / Inert atmosphere
4.3: 2 h / 0 °C / Inert atmosphere
With
carbon disulfide; dmap; titanium tetrachloride; triethylamine; potassium hydroxide;
In
dichloromethane; water;
4.3: |Aldol Condensation;
DOI:10.1021/ol3023006
