Technology Process of methyl rel-(1R,2S,12R,13S)-(5E,9E)-12-(phenylsulfonyl)-2-hydroxy-2,6,10-trimethyl-15-oxo-16-oxabicyclo<11.3.1>heptadeca-5,9-diene-12-carboxylate
There total 10 articles about methyl rel-(1R,2S,12R,13S)-(5E,9E)-12-(phenylsulfonyl)-2-hydroxy-2,6,10-trimethyl-15-oxo-16-oxabicyclo<11.3.1>heptadeca-5,9-diene-12-carboxylate 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:
-
Multi-step reaction with 8 steps
1: 87 percent / pyridine / CH2Cl2 / 0.67 h / 0 °C
2: 99 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 1.) 0 deg C, 10 min, 2.) RT, 7 h
3: 1.) LDA / 1.) THF, -78 deg C, 20 min, 2.) THF, -78 deg C, 30 min
4: 71 percent / 2 percent aq. H2SO4 / methanol / 7 h / Heating
5: 99 percent / pyridine, H2 / 15 percent palladium on barium sulfate / 2.5 h / 760 Torr
6: 10-camphorsulfonic acid / tetrahydrofuran / 2.5 h / Heating
7: 92 percent / KO-t-Bu / 2-methyl-propan-2-ol; dimethylsulfoxide / 16 h / Ambient temperature
With
pyridine; sulfuric acid; (1S)-10-camphorsulfonic acid; potassium tert-butylate; hydrogen; pyridinium p-toluenesulfonate; lithium diisopropyl amide;
Pd-BaSO4;
In
tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; tert-butyl alcohol;
DOI:10.1021/jo00388a008
- Guidance literature:
-
Multi-step reaction with 7 steps
1: 99 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 1.) 0 deg C, 10 min, 2.) RT, 7 h
2: 1.) LDA / 1.) THF, -78 deg C, 20 min, 2.) THF, -78 deg C, 30 min
3: 71 percent / 2 percent aq. H2SO4 / methanol / 7 h / Heating
4: 99 percent / pyridine, H2 / 15 percent palladium on barium sulfate / 2.5 h / 760 Torr
5: 10-camphorsulfonic acid / tetrahydrofuran / 2.5 h / Heating
6: 92 percent / KO-t-Bu / 2-methyl-propan-2-ol; dimethylsulfoxide / 16 h / Ambient temperature
With
pyridine; sulfuric acid; (1S)-10-camphorsulfonic acid; potassium tert-butylate; hydrogen; pyridinium p-toluenesulfonate; lithium diisopropyl amide;
Pd-BaSO4;
In
tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; tert-butyl alcohol;
DOI:10.1021/jo00388a008
- Guidance literature:
-
Multi-step reaction with 9 steps
1: p-TsOH / methanol / 1 h / Ambient temperature
2: 87 percent / pyridine / CH2Cl2 / 0.67 h / 0 °C
3: 99 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 1.) 0 deg C, 10 min, 2.) RT, 7 h
4: 1.) LDA / 1.) THF, -78 deg C, 20 min, 2.) THF, -78 deg C, 30 min
5: 71 percent / 2 percent aq. H2SO4 / methanol / 7 h / Heating
6: 99 percent / pyridine, H2 / 15 percent palladium on barium sulfate / 2.5 h / 760 Torr
7: 10-camphorsulfonic acid / tetrahydrofuran / 2.5 h / Heating
8: 92 percent / KO-t-Bu / 2-methyl-propan-2-ol; dimethylsulfoxide / 16 h / Ambient temperature
With
pyridine; sulfuric acid; (1S)-10-camphorsulfonic acid; potassium tert-butylate; hydrogen; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; lithium diisopropyl amide;
Pd-BaSO4;
In
tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; tert-butyl alcohol;
DOI:10.1021/jo00388a008
