Technology Process of (3beta,12R,13beta)-1,2-didehydrocrinan-3,12-diol
There total 12 articles about (3beta,12R,13beta)-1,2-didehydrocrinan-3,12-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:
-
formaldehyd; (3R,3aS,6S,7aS)-3a-(benzo[d][1,3]dioxol-5-yl)-6-hydroxy-2,3,3a,6,7,7a-hexahydro-1H-indol-3-yl acetate;
With
trifluoroacetic acid;
In
1,2-dichloro-ethane;
at 60 ℃;
for 18h;
With
potassium carbonate;
In
methanol;
at 22 ℃;
for 1h;
DOI:10.1021/acs.joc.9b00018
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; benzene / 14 h / Reflux
2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C
2.2: 1.5 h / 22 °C
3.1: N,N'-bis(benzyliden)ethylendiamine; palladium diacetate / benzene / 13 h / Reflux
4.1: citric acid; 4-methylmorpholine N-oxide; potassium osmate(VI) dihydrate / acetonitrile; water / 72 h / 22 °C
4.2: 2 h / 22 °C
5.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 10 h / -78 - 22 °C
5.2: 4 h / 22 °C
6.1: selenium(IV) oxide / 1,4-dioxane / 20 h / Reflux
7.1: naphthalene radical anion sodium salt / tetrahydrofuran / -100 °C
8.1: trifluoroacetic acid / 1,2-dichloro-ethane / 18 h / 60 °C
8.2: 1 h / 22 °C
With
selenium(IV) oxide; potassium osmate(VI) dihydrate; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium(0); N,N'-bis(benzyliden)ethylendiamine; palladium diacetate; naphthalene radical anion sodium salt; sodium hydride; sodium carbonate; 4-methylmorpholine N-oxide; trifluoroacetic acid; citric acid;
In
tetrahydrofuran; 1,4-dioxane; methanol; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile; benzene;
1.1: |Suzuki-Miyaura Coupling / 8.1: |Pictet-Spengler Synthesis;
DOI:10.1021/acs.joc.9b00018
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C
1.2: 1.5 h / 22 °C
2.1: N,N'-bis(benzyliden)ethylendiamine; palladium diacetate / benzene / 13 h / Reflux
3.1: citric acid; 4-methylmorpholine N-oxide; potassium osmate(VI) dihydrate / acetonitrile; water / 72 h / 22 °C
3.2: 2 h / 22 °C
4.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 10 h / -78 - 22 °C
4.2: 4 h / 22 °C
5.1: selenium(IV) oxide / 1,4-dioxane / 20 h / Reflux
6.1: naphthalene radical anion sodium salt / tetrahydrofuran / -100 °C
7.1: trifluoroacetic acid / 1,2-dichloro-ethane / 18 h / 60 °C
7.2: 1 h / 22 °C
With
selenium(IV) oxide; potassium osmate(VI) dihydrate; sodium tetrahydroborate; N,N'-bis(benzyliden)ethylendiamine; palladium diacetate; naphthalene radical anion sodium salt; sodium hydride; 4-methylmorpholine N-oxide; trifluoroacetic acid; citric acid;
In
tetrahydrofuran; 1,4-dioxane; methanol; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile; benzene;
7.1: |Pictet-Spengler Synthesis;
DOI:10.1021/acs.joc.9b00018
