Technology Process of (7R,8S,8aS)-8-[(2-methoxyethoxy)methoxy]-3-oxo-7-(phenylselanyl)-2,3,6,7,8,8a-hexahydrooxepino[4,3-b]pyrrole-1-carboxylic acid tert-butyl ester
There total 16 articles about (7R,8S,8aS)-8-[(2-methoxyethoxy)methoxy]-3-oxo-7-(phenylselanyl)-2,3,6,7,8,8a-hexahydrooxepino[4,3-b]pyrrole-1-carboxylic acid tert-butyl ester 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
toluene;
for 31h;
DOI:10.1021/ol071147z
- Guidance literature:
-
Multi-step reaction with 14 steps
1: Et3N / CH2Cl2 / 2.33 h / 0 - 20 °C
2: 94 percent / imidazole / CH2Cl2 / 48 h
3: 91 percent / NaBH4; CaCl2 / tetrahydrofuran; ethanol / 0 °C
4: 91 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / 0.83 h / -78 - 20 °C
5: 63 percent / t-BuLi / pentane; tetrahydrofuran / 2 h / -78 °C
6: 83 percent / i-Pr2NEt; Bu4NI / tetrahydrofuran / 20 h / Heating
7: 98 percent / ethyl acetate; H2O / 0.25 h
8: 98 percent / LiAlH4 / diethyl ether / 0.33 h / 0 °C
9: 80 percent / pyridine; DMAP / CH2Cl2 / 3.5 h
10: 95 percent / Bu4NF; AcOH / tetrahydrofuran / 2 h
11: 40 percent / DMSO; (COCl)2; Et3N / CH2Cl2 / 1 h / -78 °C
12: 64 percent / K2CO3 / methanol; H2O / 0.5 h
13: 53 percent / tetrahydrofuran / 24 h / Heating
14: 61 percent / CF3COOH / toluene / 31 h
With
pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; tetrabutyl ammonium fluoride; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; calcium chloride;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; toluene; pentane;
4: Swern oxidation / 11: Swern oxidation;
DOI:10.1021/ol071147z
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 98 percent / ethyl acetate; H2O / 0.25 h
2: 98 percent / LiAlH4 / diethyl ether / 0.33 h / 0 °C
3: 80 percent / pyridine; DMAP / CH2Cl2 / 3.5 h
4: 95 percent / Bu4NF; AcOH / tetrahydrofuran / 2 h
5: 40 percent / DMSO; (COCl)2; Et3N / CH2Cl2 / 1 h / -78 °C
6: 64 percent / K2CO3 / methanol; H2O / 0.5 h
7: 53 percent / tetrahydrofuran / 24 h / Heating
8: 61 percent / CF3COOH / toluene / 31 h
With
pyridine; dmap; lithium aluminium tetrahydride; oxalyl dichloride; tetrabutyl ammonium fluoride; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; trifluoroacetic acid;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; toluene;
5: Swern oxidation;
DOI:10.1021/ol071147z
![(2S)-3-dimethylaminomethylene-2-[(1S,2R)-3-hydroxy-1-[(2-methoxyethoxy)methoxy]-2-(phenylselanyl)propyl]-4-oxopyrrolidine-1-carboxylic acid tert-butyl ester](/Databaselist/images/loading.webp)
