Technology Process of (3E,6S,9E,11S,14S)-11-hydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,5,8-trione
There total 28 articles about (3E,6S,9E,11S,14S)-11-hydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,5,8-trione 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
trifluoroacetic acid;
In
dichloromethane;
at 0 - 25 ℃;
for 2h;
Inert atmosphere;
DOI:10.1055/s-0033-1339121
- Guidance literature:
-
Multi-step reaction with 12 steps
1: D-Prolin / dimethyl sulfoxide / 0.42 h / 20 °C
2: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / 1 h / 0 °C
3: copper(ll) sulfate pentahydrate / methanol / 12 h / 20 °C
4: N-ethyl-N,N-diisopropylamine / dichloromethane / 5 h / 20 °C
5: lithium hydroxide monohydrate / tetrahydrofuran; water / 8 h / 20 °C
6: dicyclohexyl-carbodiimide; dmap / dichloromethane / 12 h / 0 °C
7: toluene-4-sulfonic acid / methanol / 0.5 h / 0 °C
8: triethylamine / dichloromethane / 1 h / 0 °C
9: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / 50 °C
10: Hoveyda-Grubbs catalyst second generation / toluene / 0.5 h / 80 °C / Inert atmosphere
11: Dess-Martin periodane / dichloromethane / 5 h / 20 °C
12: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
With
dmap; Hoveyda-Grubbs catalyst second generation; copper(ll) sulfate pentahydrate; lithium hydroxide monohydrate; Dess-Martin periodane; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; D-Prolin; lithium chloride;
In
tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; toluene;
2: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1002/hlca.201200631
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: potassium carbonate / methanol / 3 h / 25 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -20 °C
2.2: 4 h / -20 °C
3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 - 25 °C / Inert atmosphere
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 25 °C
5.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 3 h / 0 - 25 °C / Inert atmosphere
6.1: acetic acid / water / 24 h / 25 °C
7.1: toluene-4-sulfonic acid; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / Dichlorofluoromethane / 0.75 h / 0 °C
8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C
9.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 4 h / 25 - 40 °C / Inert atmosphere
10.1: trifluoroacetic acid / dichloromethane / 2 h / 0 - 25 °C / Inert atmosphere
With
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl ammonium fluoride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid;
In
tetrahydrofuran; methanol; hexane; dichloromethane; Dichlorofluoromethane; water;
DOI:10.1055/s-0033-1339121
