Technology Process of (2S,3S,4R)-4-Benzyloxy-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-(3,5-dimethoxy-2-methoxymethoxy-4-methyl-phenyl)-ethyl]-3-methanesulfonyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester
There total 14 articles about (2S,3S,4R)-4-Benzyloxy-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-(3,5-dimethoxy-2-methoxymethoxy-4-methyl-phenyl)-ethyl]-3-methanesulfonyloxy-pyrrolidine-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:
-
Multi-step reaction with 9 steps
1.1: 30.4 g / Et3N / CH2Cl2 / 4 h / 25 °C
2.1: 86 percent / Et3Al / NiCl2(dppp) / toluene / 0 - 25 °C
3.1: 72 percent / PhIO; I2 / CH2Cl2 / 24 h / 25 °C
4.1: 97 percent / K2CO3 / methanol; H2O / 4 h / 20 °C
5.1: NaH; n-Bu4NI / tetrahydrofuran; dimethylformamide / 0.5 h / 0 °C
5.2: 89 percent / tetrahydrofuran; dimethylformamide / 1 h / 0 °C
6.1: SmI2; n-Bu3SnCl / Pd(PPh3)4 / tetrahydrofuran / 12 h / 25 °C
6.2: 1.22 g / BF3*OEt2 / CH2Cl2 / 0.5 h / -78 °C
7.1: O3 / methanol / 0.5 h / -78 °C
7.2: 62 percent / NaBH4 / methanol / 1 h / 0 °C
8.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 3 h / 25 °C
9.1: 76 percent / pyridine / CH2Cl2 / 0 °C
With
pyridine; dmap; samarium diiodide; iodosylbenzene; tributyltin chloride; iodine; triethylaluminum; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; ozone; triethylamine;
tetrakis(triphenylphosphine) palladium(0); 1,3-bis[(diphenylphosphino)propane]dichloronickel(II);
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo048924i
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: NaH / tetrahydrofuran; dimethylformamide / 1 h / 25 °C
1.2: 89 percent / tetrahydrofuran; dimethylformamide / 1 h / 25 °C
2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 0 °C
2.2: 86 percent / tetrahydrofuran; hexane / 0 - 25 °C
3.1: 89 percent / Et3N; 4-(N,N-dimethylamino)pyridine / CH2Cl2 / 3 h / 25 °C
4.1: SmI2; n-Bu3SnCl / Pd(PPh3)4 / tetrahydrofuran / 12 h / 25 °C
4.2: 1.22 g / BF3*OEt2 / CH2Cl2 / 0.5 h / -78 °C
5.1: O3 / methanol / 0.5 h / -78 °C
5.2: 62 percent / NaBH4 / methanol / 1 h / 0 °C
6.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 3 h / 25 °C
7.1: 76 percent / pyridine / CH2Cl2 / 0 °C
With
pyridine; dmap; n-butyllithium; samarium diiodide; tributyltin chloride; sodium hydride; ozone; triethylamine;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo048924i
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: m-CPBA / CH2Cl2 / 3 h / 0 °C
1.2: 87 percent / KOH / methanol / 1 h / 0 °C
2.1: NaH / tetrahydrofuran; dimethylformamide / 1 h / 25 °C
2.2: 89 percent / tetrahydrofuran; dimethylformamide / 1 h / 25 °C
3.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 0 °C
3.2: 86 percent / tetrahydrofuran; hexane / 0 - 25 °C
4.1: 89 percent / Et3N; 4-(N,N-dimethylamino)pyridine / CH2Cl2 / 3 h / 25 °C
5.1: SmI2; n-Bu3SnCl / Pd(PPh3)4 / tetrahydrofuran / 12 h / 25 °C
5.2: 1.22 g / BF3*OEt2 / CH2Cl2 / 0.5 h / -78 °C
6.1: O3 / methanol / 0.5 h / -78 °C
6.2: 62 percent / NaBH4 / methanol / 1 h / 0 °C
7.1: 99 percent / Et3N; 4-(dimethylamino)pyridine / CH2Cl2 / 3 h / 25 °C
8.1: 76 percent / pyridine / CH2Cl2 / 0 °C
With
pyridine; dmap; n-butyllithium; samarium diiodide; tributyltin chloride; sodium hydride; ozone; triethylamine; 3-chloro-benzenecarboperoxoic acid;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
1.1: Baeyer-Villiger oxidation;
DOI:10.1021/jo048924i
