Technology Process of (1R,3S,4S,11S)-8,16-bis(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-4-(dimethylamino)-12-hydroxy-18-(1-methylpyrrolidin-2-yl)-19-(trifluoromethyl)-6-oxa-7-azapentacyclo[11.8.0.03,11.05,9.015,20]henicosa-5(9),7,12,15(20),16,18-hexaene-10,14-dione
There total 18 articles about (1R,3S,4S,11S)-8,16-bis(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-4-(dimethylamino)-12-hydroxy-18-(1-methylpyrrolidin-2-yl)-19-(trifluoromethyl)-6-oxa-7-azapentacyclo[11.8.0.03,11.05,9.015,20]henicosa-5(9),7,12,15(20),16,18-hexaene-10,14-dione 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:
-
![(1R,3S,4S,11S)-8,16-bis(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-4-(dimethylamino)-12-hydroxy-18-(1-methylpyrrolidin-2-yl)-19-(trifluoromethyl)-6-oxa-7-azapentacyclo[11.8.0.0<sup>3,11</sup>.0<sup>5,9</sup>.0<sup>15,20</sup>]henicosa-5<sup>(9)</sup>,7,12,15<sup>(20)</sup>,16,18-hexaene-10,14-dione](/Databaselist/images/loading.webp)
-
1359023-04-3
(1R,3S,4S,11S)-8,16-bis(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-4-(dimethylamino)-12-hydroxy-18-(1-methylpyrrolidin-2-yl)-19-(trifluoromethyl)-6-oxa-7-azapentacyclo[11.8.0.03,11.05,9.015,20]henicosa-5(9),7,12,15(20),16,18-hexaene-10,14-dione
- Guidance literature:
-
phenyl 6-(benzyloxy)-2-methyl-4-(1-methylpyrrolidin-2-yl)-3-(trifluoromethyl)benzoate;
With
N,N,N,N,-tetramethylethylenediamine; lithium diisopropyl amide;
In
tetrahydrofuran;
at -78 ℃;
for 0.5h;
(4aS,8aS,9S)-3-(benzyloxy)-4a-(tert-butyldimethylsilyloxy)-9-(dimethylamino)-8a,9-dihydronaphtho[2,3-d]isoxazole-4,5(4aH,8H)-dione;
In
tetrahydrofuran;
at -50 ℃;
-
-
1359023-04-3
(1R,3S,4S,11S)-8,16-bis(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-4-(dimethylamino)-12-hydroxy-18-(1-methylpyrrolidin-2-yl)-19-(trifluoromethyl)-6-oxa-7-azapentacyclo[11.8.0.03,11.05,9.015,20]henicosa-5(9),7,12,15(20),16,18-hexaene-10,14-dione
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: potassium carbonate / acetone / 20 °C
2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -100 °C / Inert atmosphere
2.2: 3 h / -78 °C / Inert atmosphere
3.1: acetic acid; triacetoxy sodium borohydride / 1,2-dichloro-ethane / 20 °C
4.1: dmap / N,N-dimethyl-formamide / 2 h / 20 °C
5.1: silver trifluoroacetate; iodine / chloroform / 2.5 h / 20 °C
6.1: copper(l) iodide / N,N-dimethyl-formamide / 44 h / 80 °C / Sealed tube
7.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C
8.1: acetic acid / water; 1,2-dichloro-ethane / 0.33 h / 20 °C
8.2: 20 °C
9.1: lithium diisopropyl amide; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / 0.5 h / -78 °C
9.2: -78 - -50 °C
9.3: -50 - -5 °C
With
hydrogenchloride; dmap; copper(l) iodide; n-butyllithium; triacetoxy sodium borohydride; N,N,N,N,-tetramethylethylenediamine; iodine; silver trifluoroacetate; potassium carbonate; acetic acid; lithium diisopropyl amide;
In
tetrahydrofuran; 1,4-dioxane; chloroform; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/acs.jmedchem.6b01903
-
-
1359023-04-3
(1R,3S,4S,11S)-8,16-bis(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-4-(dimethylamino)-12-hydroxy-18-(1-methylpyrrolidin-2-yl)-19-(trifluoromethyl)-6-oxa-7-azapentacyclo[11.8.0.03,11.05,9.015,20]henicosa-5(9),7,12,15(20),16,18-hexaene-10,14-dione
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / toluene; 1,4-dioxane; water / 2 h / 90 °C / Inert atmosphere
2.1: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 20 °C / 760.05 Torr
3.1: potassium carbonate / acetone / 20 °C
4.1: silver trifluoroacetate; iodine / chloroform / 2.5 h / 20 °C
5.1: copper(l) iodide / N,N-dimethyl-formamide / 44 h / 80 °C / Sealed tube
6.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C
7.1: acetic acid / water; 1,2-dichloro-ethane / 0.33 h / 20 °C
7.2: 20 °C
8.1: lithium diisopropyl amide; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / 0.5 h / -78 °C
8.2: -78 - -50 °C
8.3: -50 - -5 °C
With
hydrogenchloride; copper(l) iodide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; N,N,N,N,-tetramethylethylenediamine; palladium 10% on activated carbon; hydrogen; iodine; silver trifluoroacetate; sodium carbonate; potassium carbonate; acetic acid; lithium diisopropyl amide;
In
tetrahydrofuran; 1,4-dioxane; methanol; chloroform; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; toluene;
1.1: |Suzuki Coupling;
DOI:10.1021/acs.jmedchem.6b01903
