(1R,3S,4S,11S)-8-(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-4-(dimethylamino)-19-fluoro-12-hydroxy-10,14-dioxo-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-hexaen-16-yl tert-butyl carbonate

Base Information

• Chemical Name: (1R,3S,4S,11S)-8-(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-4-(dimethylamino)-19-fluoro-12-hydroxy-10,14-dioxo-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-hexaen-16-yl tert-butyl carbonate
• CAS No.: 1207283-57-5
• Molecular Formula: C₃₉H₄₇FN₂O₉Si
• Molecular Weight: 734.894

Synonyms:(1R,3S,4S,11S)-8-(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-4-(dimethylamino)-19-fluoro-12-hydroxy-10,14-dioxo-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-hexaen-16-yl tert-butyl carbonate

Chemical Property of (1R,3S,4S,11S)-8-(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-4-(dimethylamino)-19-fluoro-12-hydroxy-10,14-dioxo-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-hexaen-16-yl tert-butyl carbonate

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Technology Process of (1R,3S,4S,11S)-8-(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-4-(dimethylamino)-19-fluoro-12-hydroxy-10,14-dioxo-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-hexaen-16-yl tert-butyl carbonate

There total 6 articles about (1R,3S,4S,11S)-8-(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-4-(dimethylamino)-19-fluoro-12-hydroxy-10,14-dioxo-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-hexaen-16-yl tert-butyl carbonate 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: 35.0%

(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) + phenyl 6-{[(tert-butoxy)carbonyl]oxy}-3-fluoro-2-methylbenzoate (1207283-56-4) → (1R,3S,4S,11S)-8-(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-4-(dimethylamino)-19-fluoro-12-hydroxy-10,14-dioxo-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-hexaen-16-yl tert-butyl carbonate (1207283-57-5)

Guidance literature:

phenyl 6-{[(tert-butoxy)carbonyl]oxy}-3-fluoro-2-methylbenzoate; With N,N,N,N,-tetramethylethylenediamine; lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.0833333h;

(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 -78 - 25 ℃;

With water; ammonium chloride; In tetrahydrofuran;

Reference yield:

3-fluoro-6-methoxy-2-methylbenzoic acid (220901-72-4) → (1R,3S,4S,11S)-8-(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-4-(dimethylamino)-19-fluoro-12-hydroxy-10,14-dioxo-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-hexaen-16-yl tert-butyl carbonate (1207283-57-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 1 h / 25 °C

2.1: dmap; triethylamine / dichloromethane / 12 h / 25 °C

3.1: boron tribromide / dichloromethane / 1.5 h / -78 - 25 °C

4.1: dmap / dichloromethane / 1.5 h / 25 °C

5.1: N,N,N,N,-tetramethylethylenediamine; lithium diisopropyl amide / tetrahydrofuran; hexane / 0.08 h / -78 °C / Large scale reaction

5.2: 1 h / -78 - 25 °C

With dmap; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; boron tribromide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm201465w

Reference yield:

phenyl 3-fluoro-6-methoxy-2-methylbenzoate (1207283-54-2) → (1R,3S,4S,11S)-8-(benzyloxy)-11-[(tert-butyldimethylsilyl)oxy]-4-(dimethylamino)-19-fluoro-12-hydroxy-10,14-dioxo-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-hexaen-16-yl tert-butyl carbonate (1207283-57-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: boron tribromide / dichloromethane / 1.5 h / -78 - 25 °C

2.1: dmap / dichloromethane / 1.5 h / 25 °C

3.1: N,N,N,N,-tetramethylethylenediamine; lithium diisopropyl amide / tetrahydrofuran; hexane / 0.08 h / -78 °C / Large scale reaction

3.2: 1 h / -78 - 25 °C

With dmap; N,N,N,N,-tetramethylethylenediamine; boron tribromide; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jm201465w

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-{[(tert-butoxy)carbonyl]oxy}-3-fluoro-2-methylbenzoate

phenyl 3-fluoro-6-hydroxy-2-methylbenzoate

3-fluoro-6-methoxy-2-methylbenzoic acid

Downstream raw materials:

(1R,3S,4S,11S)-8-(benzyloxy)-4-(dimethylamino)-19-fluoro-11,12,16-trihydroxy-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

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