Technology Process of (4S,5S,8S,9S,10S,13S,14R,17S)-4-(tert-Butyl-diphenyl-silanyloxy)-17-hydroxy-13-methyl-1,7-dioxo-hexadecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl ester
There total 8 articles about (4S,5S,8S,9S,10S,13S,14R,17S)-4-(tert-Butyl-diphenyl-silanyloxy)-17-hydroxy-13-methyl-1,7-dioxo-hexadecahydro-cyclopenta[a]phenanthrene-10-carboxylic acid methyl 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:
-
3-((1S,3aS,7aS)-1-Methoxymethoxy-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl)-3-oxo-propionic acid allyl ester; (4S)-4-t-butyldiphenylsilyloxy-2-carbomethoxycyclohex-2-en-1-one;
With
caesium carbonate;
In
dichloromethane;
at 20 ℃;
for 18h;
With
morpholine;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran;
at 20 ℃;
for 3h;
With
hydrogenchloride;
In
methanol;
for 0.25h;
Further stages.;
Heating;
DOI:10.1021/ol017274r
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: 79 percent / oxalyl chloride; methyl sulfoxide; triethylamine / CH2Cl2 / 105 h / -78 - 20 °C
2.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 2 h / -78 °C
2.2: 60 percent / tetrahydrofuran / 3 h / -30 °C
3.1: 67 percent / K2CO3 / PdCl2(PPh3)2 / tetrahydrofuran / 18 h / 20 °C
4.1: n-BuLi; diisopropylamine / tetrahydrofuran / 0.17 h / -78 °C
4.2: tetrahydrofuran / 4 h / -78 - 0 °C
5.1: DMAP / toluene / 2 h / Heating
6.1: Cs2CO3 / CH2Cl2 / 18 h / 20 °C
6.2: morpholine / Pd(PPh3)4 / tetrahydrofuran / 3 h / 20 °C
6.3: HCl / methanol / 0.25 h / Heating
With
dmap; n-butyllithium; oxalyl dichloride; potassium carbonate; caesium carbonate; dimethyl sulfoxide; triethylamine; diisopropylamine;
bis-triphenylphosphine-palladium(II) chloride;
In
tetrahydrofuran; dichloromethane; toluene;
1.1: Swern oxidation reaction;
DOI:10.1021/ol017274r
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: 82 percent / (i-Pr)2NEt / CH2Cl2 / 18 h / 20 °C
2.1: diborane / tetrahydrofuran / 18 h / 20 °C
2.2: 71 percent / NaOH; H2O2 / tetrahydrofuran; H2O / 4 h / 20 °C
3.1: 79 percent / oxalyl chloride; methyl sulfoxide; triethylamine / CH2Cl2 / 105 h / -78 - 20 °C
4.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 2 h / -78 °C
4.2: 60 percent / tetrahydrofuran / 3 h / -30 °C
5.1: 67 percent / K2CO3 / PdCl2(PPh3)2 / tetrahydrofuran / 18 h / 20 °C
6.1: n-BuLi; diisopropylamine / tetrahydrofuran / 0.17 h / -78 °C
6.2: tetrahydrofuran / 4 h / -78 - 0 °C
7.1: DMAP / toluene / 2 h / Heating
8.1: Cs2CO3 / CH2Cl2 / 18 h / 20 °C
8.2: morpholine / Pd(PPh3)4 / tetrahydrofuran / 3 h / 20 °C
8.3: HCl / methanol / 0.25 h / Heating
With
dmap; n-butyllithium; oxalyl dichloride; potassium carbonate; caesium carbonate; dimethyl sulfoxide; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; diborane;
bis-triphenylphosphine-palladium(II) chloride;
In
tetrahydrofuran; dichloromethane; toluene;
3.1: Swern oxidation reaction;
DOI:10.1021/ol017274r
