Technology Process of (1R,3S,4S,11S)-8,16-bis(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-19-chloro-4-(dimethylamino)-12-hydroxy-18-(pyrrolidin-2-yl)-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 9 articles about (1R,3S,4S,11S)-8,16-bis(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-19-chloro-4-(dimethylamino)-12-hydroxy-18-(pyrrolidin-2-yl)-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:
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![(1R,3S,4S,11S)-8,16-bis(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-19-chloro-4-(dimethylamino)-12-hydroxy-18-(pyrrolidin-2-yl)-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)
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1359022-63-1
(1R,3S,4S,11S)-8,16-bis(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-19-chloro-4-(dimethylamino)-12-hydroxy-18-(pyrrolidin-2-yl)-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:
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phenyl 6-(benzyloxy)-3-chloro-2-methyl-4-(pyrrolidin-2-yl)benzoate;
With
n-butyllithium; N,N,N,N,-tetramethylethylenediamine; diisopropylamine;
In
tetrahydrofuran; hexane;
at -78 ℃;
for 1h;
Inert atmosphere;
(4aS,8aS,9S)-3-(benzyloxy)-4a-(tert-butyldimethylsilyloxy)-9-(dimethylamino)-8a,9-dihydronaphtho[2,3-d]isoxazole-4,5(4aH,8H)-dione;
In
tetrahydrofuran; hexane;
at -100 - -78 ℃;
Inert atmosphere;
With
lithium hexamethyldisilazane;
In
tetrahydrofuran; hexane;
at -78 - -5 ℃;
Inert atmosphere;
DOI:10.1021/acs.jmedchem.6b01903
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1359022-63-1
(1R,3S,4S,11S)-8,16-bis(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-19-chloro-4-(dimethylamino)-12-hydroxy-18-(pyrrolidin-2-yl)-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:
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Multi-step reaction with 4 steps
1.1: potassium carbonate / acetone / 20 °C
2.1: N-chloro-succinimide / acetonitrile / 18 h / 60 °C
3.1: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C
4.1: n-butyllithium; diisopropylamine; N,N,N,N,-tetramethylethylenediamine / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
4.2: -100 - -78 °C / Inert atmosphere
4.3: -78 - -5 °C / Inert atmosphere
With
hydrogenchloride; N-chloro-succinimide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; potassium carbonate; diisopropylamine;
In
tetrahydrofuran; 1,4-dioxane; hexane; acetone; acetonitrile;
DOI:10.1021/acs.jmedchem.6b01903
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-
1359022-63-1
(1R,3S,4S,11S)-8,16-bis(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-19-chloro-4-(dimethylamino)-12-hydroxy-18-(pyrrolidin-2-yl)-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 6 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: N-chloro-succinimide / acetonitrile / 18 h / 60 °C
5.1: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C
6.1: n-butyllithium; diisopropylamine; N,N,N,N,-tetramethylethylenediamine / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
6.2: -100 - -78 °C / Inert atmosphere
6.3: -78 - -5 °C / Inert atmosphere
With
hydrogenchloride; N-chloro-succinimide; n-butyllithium; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; N,N,N,N,-tetramethylethylenediamine; palladium 10% on activated carbon; hydrogen; sodium carbonate; potassium carbonate; diisopropylamine;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; water; acetone; toluene; acetonitrile;
1.1: |Suzuki Coupling;
DOI:10.1021/acs.jmedchem.6b01903
