(1R,3S,4S,11S)-8,16-bis(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-19-chloro-4-(dimethylamino)-12-hydroxy-18-(pyridin-4-yl)-6-oxa-7-azapentacyclo[11.8.0.0^3,11.0^5,9.0^15,20]henicosa-5⁽⁹⁾,7,12,15⁽²⁰⁾,16,18-hexaene-10,14-dione

Base Information

• Chemical Name: (1R,3S,4S,11S)-8,16-bis(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-19-chloro-4-(dimethylamino)-12-hydroxy-18-(pyridin-4-yl)-6-oxa-7-azapentacyclo[11.8.0.0^3,11.0^5,9.0^15,20]henicosa-5⁽⁹⁾,7,12,15⁽²⁰⁾,16,18-hexaene-10,14-dione
• CAS No.: 1359022-56-2
• Molecular Formula: C₄₆H₄₈ClN₃O₇Si
• Molecular Weight: 818.442

Synonyms:

Chemical Property of (1R,3S,4S,11S)-8,16-bis(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-19-chloro-4-(dimethylamino)-12-hydroxy-18-(pyridin-4-yl)-6-oxa-7-azapentacyclo[11.8.0.0^3,11.0^5,9.0^15,20]henicosa-5⁽⁹⁾,7,12,15⁽²⁰⁾,16,18-hexaene-10,14-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (1R,3S,4S,11S)-8,16-bis(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-19-chloro-4-(dimethylamino)-12-hydroxy-18-(pyridin-4-yl)-6-oxa-7-azapentacyclo[11.8.0.0^3,11.0^5,9.0^15,20]henicosa-5⁽⁹⁾,7,12,15⁽²⁰⁾,16,18-hexaene-10,14-dione

There total 4 articles about (1R,3S,4S,11S)-8,16-bis(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-19-chloro-4-(dimethylamino)-12-hydroxy-18-(pyridin-4-yl)-6-oxa-7-azapentacyclo[11.8.0.0^3,11.0^5,9.0^15,20]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:

Reference yield:

phenyl 6-(benzyloxy)-4-bromo-3-chloro-2-methylbenzoate (1254340-87-8) → (1R,3S,4S,11S)-8,16-bis(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-19-chloro-4-(dimethylamino)-12-hydroxy-18-(pyridin-4-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 (1359022-56-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium; diisopropylamine; N,N,N,N,-tetramethylethylenediamine / hexane; tetrahydrofuran / -78 - -70 °C / Inert atmosphere

1.2: -100 - -78 °C / Inert atmosphere

1.3: 1 h / -78 - -5 °C / Inert atmosphere

2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / toluene; 1,4-dioxane; water / 1 h / Inert atmosphere; Heating

With n-butyllithium; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; N,N,N,N,-tetramethylethylenediamine; sodium carbonate; diisopropylamine; In tetrahydrofuran; 1,4-dioxane; hexane; water; toluene; 2.1: |Suzuki Coupling;

DOI:10.1021/acs.jmedchem.6b01903

Reference yield:

(4aS,8aS,9S)-3-(benzyloxy)-4a-(tert-butyldimethylsilyloxy)-9-(dimethylamino)-8a,9-dihydronaphtho[2,3-d]isoxazole-4,5(4aH,8H)-dione (852821-06-8) → (1R,3S,4S,11S)-8,16-bis(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-19-chloro-4-(dimethylamino)-12-hydroxy-18-(pyridin-4-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 (1359022-56-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium; diisopropylamine; N,N,N,N,-tetramethylethylenediamine / hexane; tetrahydrofuran / -78 - -70 °C / Inert atmosphere

1.2: -100 - -78 °C / Inert atmosphere

1.3: 1 h / -78 - -5 °C / Inert atmosphere

2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / toluene; 1,4-dioxane; water / 1 h / Inert atmosphere; Heating

With n-butyllithium; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; N,N,N,N,-tetramethylethylenediamine; sodium carbonate; diisopropylamine; In tetrahydrofuran; 1,4-dioxane; hexane; water; toluene; 2.1: |Suzuki Coupling;

DOI:10.1021/acs.jmedchem.6b01903

Reference yield:

(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 (1359022-51-7) + 4-pyridylboronic acid (1692-15-5) → (1R,3S,4S,11S)-8,16-bis(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-19-chloro-4-(dimethylamino)-12-hydroxy-18-(pyridin-4-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 (1359022-56-2)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate; In 1,4-dioxane; water; toluene; for 1h; Inert atmosphere; Heating;

DOI:10.1021/acs.jmedchem.6b01903

upstream raw materials:

(4aS,8aS,9S)-3-(benzyloxy)-4a-(tert-butyldimethylsilyloxy)-9-(dimethylamino)-8a,9-dihydronaphtho[2,3-d]isoxazole-4,5(4aH,8H)-dione

phenyl 6-(benzyloxy)-4-bromo-3-chloro-2-methylbenzoate

(1R,3S,4S,11S)-8,16-bis(benzyloxy)-18-bromo-11-[(tertbutyldimethylsilyl)oxy]-19-chloro-4-(dimethylamino)-12-hydroxy-6-oxa-7-azapentacyclo[11.8.0.0^3,11.0^5,9.0^15,20]henicosa-5⁽⁹⁾,7,12,15⁽²⁰⁾,16,18-hexaene-10,14-dione

4-pyridylboronic acid

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