Technology Process of N-<(phenyloxy)carbonyl>-2-<3-<(tert-butyldiphenylsilyl)oxy>propynyl>-6a,10a-epoxy-6-ethynyl-10-oxo-5,6,6a,7,8,9,10,10a-octahydrophenanthridine
There total 10 articles about N-<(phenyloxy)carbonyl>-2-<3-<(tert-butyldiphenylsilyl)oxy>propynyl>-6a,10a-epoxy-6-ethynyl-10-oxo-5,6,6a,7,8,9,10,10a-octahydrophenanthridine 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 10 steps
1: 100 percent / pyridine / 24 h / 0 °C
2: 97 percent / diethylamine, copper(I) iodide, bis(triphenylphosphine)palladium(II) chloride / dimethylformamide / 11 h
3: 91 percent / m-CPBA / CH2Cl2 / 1 h / 25 °C
4: 91 percent / 1 h / 70 °C
5: 69 percent / Dowex 1*8-200 / methanol / 24 h / 60 °C
6: 88 percent / 2,6-lutidine / CH2Cl2 / 0.25 h / 0 °C
7: 1.) THF, from -78 deg C to 0 deg C, 2.) THF, from -78 deg C to 0 deg C, 2 h
8: 87 percent / m-CPBA, buffer solution (pH 7.5) / CH2Cl2 / 2 h / 25 °C
9: 92 percent / HF, Pyr / tetrahydrofuran / 24 h / 25 °C
10: 90 percent / pyridinium chlorochromate (PCC), molecular sieves 4A / CH2Cl2 / 3 h / 25 °C
With
pyridine; 2,6-dimethylpyridine; copper(l) iodide; bis(triphenylphosphine)palladium(II)-chloride; 4 A molecular sieve; buffer solution; Dowex 1*8-200; hydrogen fluoride; diethylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00049a022
- Guidance literature:
-
Multi-step reaction with 11 steps
1: sodium ethanethiolate / dimethylformamide / 4 h / 160 °C
2: 100 percent / pyridine / 24 h / 0 °C
3: 97 percent / diethylamine, copper(I) iodide, bis(triphenylphosphine)palladium(II) chloride / dimethylformamide / 11 h
4: 91 percent / m-CPBA / CH2Cl2 / 1 h / 25 °C
5: 91 percent / 1 h / 70 °C
6: 69 percent / Dowex 1*8-200 / methanol / 24 h / 60 °C
7: 88 percent / 2,6-lutidine / CH2Cl2 / 0.25 h / 0 °C
8: 1.) THF, from -78 deg C to 0 deg C, 2.) THF, from -78 deg C to 0 deg C, 2 h
9: 87 percent / m-CPBA, buffer solution (pH 7.5) / CH2Cl2 / 2 h / 25 °C
10: 92 percent / HF, Pyr / tetrahydrofuran / 24 h / 25 °C
11: 90 percent / pyridinium chlorochromate (PCC), molecular sieves 4A / CH2Cl2 / 3 h / 25 °C
With
pyridine; 2,6-dimethylpyridine; copper(l) iodide; bis(triphenylphosphine)palladium(II)-chloride; 4 A molecular sieve; buffer solution; Dowex 1*8-200; hydrogen fluoride; diethylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; sodium thioethylate;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00049a022
- Guidance literature:
-
Multi-step reaction with 9 steps
1: 97 percent / diethylamine, copper(I) iodide, bis(triphenylphosphine)palladium(II) chloride / dimethylformamide / 11 h
2: 91 percent / m-CPBA / CH2Cl2 / 1 h / 25 °C
3: 91 percent / 1 h / 70 °C
4: 69 percent / Dowex 1*8-200 / methanol / 24 h / 60 °C
5: 88 percent / 2,6-lutidine / CH2Cl2 / 0.25 h / 0 °C
6: 1.) THF, from -78 deg C to 0 deg C, 2.) THF, from -78 deg C to 0 deg C, 2 h
7: 87 percent / m-CPBA, buffer solution (pH 7.5) / CH2Cl2 / 2 h / 25 °C
8: 92 percent / HF, Pyr / tetrahydrofuran / 24 h / 25 °C
9: 90 percent / pyridinium chlorochromate (PCC), molecular sieves 4A / CH2Cl2 / 3 h / 25 °C
With
pyridine; 2,6-dimethylpyridine; copper(l) iodide; bis(triphenylphosphine)palladium(II)-chloride; 4 A molecular sieve; buffer solution; Dowex 1*8-200; hydrogen fluoride; diethylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00049a022
