Technology Process of (1R,3S,4S,11S)-8,16-bis(benzyloxy)-18-bromo-11-[(tertbutyldimethylsilyl)oxy]-19-chloro-4-(dimethylamino)-12-hydroxy-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 11 articles about (1R,3S,4S,11S)-8,16-bis(benzyloxy)-18-bromo-11-[(tertbutyldimethylsilyl)oxy]-19-chloro-4-(dimethylamino)-12-hydroxy-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)-18-bromo-11-[(tertbutyldimethylsilyl)oxy]-19-chloro-4-(dimethylamino)-12-hydroxy-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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1359022-51-7
(1R,3S,4S,11S)-8,16-bis(benzyloxy)-18-bromo-11-[(tertbutyldimethylsilyl)oxy]-19-chloro-4-(dimethylamino)-12-hydroxy-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)-4-bromo-3-chloro-2-methylbenzoate;
With
n-butyllithium; N,N,N,N,-tetramethylethylenediamine; diisopropylamine;
In
tetrahydrofuran; hexane;
at -78 - -70 ℃;
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 ℃;
for 1h;
Inert atmosphere;
DOI:10.1021/acs.jmedchem.6b01903
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1359022-51-7
(1R,3S,4S,11S)-8,16-bis(benzyloxy)-18-bromo-11-[(tertbutyldimethylsilyl)oxy]-19-chloro-4-(dimethylamino)-12-hydroxy-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 10 steps
1.1: bromine; acetic acid / methanol / 2 h / 20 °C / Cooling with ice
2.1: hydrogenchloride; sodium nitrite / water / 0.5 h / 0 °C
2.2: 4 h / 0 - 50 °C
3.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / -78 - 20 °C
3.2: 1 h / 20 °C
4.1: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 0.5 h / 20 °C
4.2: pH 1
5.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C
6.1: triethylamine / dmap / 1 h / 20 °C
7.1: N-chloro-succinimide / acetonitrile / 45 h / 60 °C
8.1: boron tribromide / dichloromethane / 0.75 h / -78 - 0 °C
8.2: 0.17 h / 20 °C
9.1: potassium carbonate / acetone / 20 °C
10.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine; diisopropylamine / tetrahydrofuran; hexanes / 1 h / -78 °C / Inert atmosphere
10.2: -100 - -78 °C
With
hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; N-chloro-succinimide; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; bromine; boron tribromide; diisobutylaluminium hydride; potassium carbonate; acetic acid; triethylamine; diisopropylamine; sodium nitrite;
dmap; N,N-dimethyl-formamide;
In
tetrahydrofuran; methanol; hexanes; dichloromethane; water; acetone; toluene; acetonitrile; tert-butyl alcohol;
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-
1359022-51-7
(1R,3S,4S,11S)-8,16-bis(benzyloxy)-18-bromo-11-[(tertbutyldimethylsilyl)oxy]-19-chloro-4-(dimethylamino)-12-hydroxy-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: diisobutylaluminium hydride / tetrahydrofuran; toluene / -78 - 20 °C
1.2: 1 h / 20 °C
2.1: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 0.5 h / 20 °C
2.2: pH 1
3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C
4.1: triethylamine / dmap / 1 h / 20 °C
5.1: N-chloro-succinimide / acetonitrile / 45 h / 60 °C
6.1: boron tribromide / dichloromethane / 0.75 h / -78 - 0 °C
6.2: 0.17 h / 20 °C
7.1: potassium carbonate / acetone / 20 °C
8.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine; diisopropylamine / tetrahydrofuran; hexanes / 1 h / -78 °C / Inert atmosphere
8.2: -100 - -78 °C
With
sodium chlorite; sodium dihydrogenphosphate; N-chloro-succinimide; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; boron tribromide; diisobutylaluminium hydride; potassium carbonate; triethylamine; diisopropylamine;
dmap; N,N-dimethyl-formamide;
In
tetrahydrofuran; hexanes; dichloromethane; water; acetone; toluene; acetonitrile; tert-butyl alcohol;
