N-[(4aS,11aR,12aS,13S)-13-(dimethylamino)-4a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-10-fluoro-4,4a,6,11,11a,12,12a,13-octahydro-5-hydroxy-4,6-dioxo-3,7-bis(phenylmethoxy)isoxazolo[5',4';6,7]naphth[2,3-g]isoquinolin-8-yl]-N-[3-(dimethylamino)-2,2-dimethylpropyl]-carbamic acid phenylmethyl ester

Base Information

Chemical Name:N-[(4aS,11aR,12aS,13S)-13-(dimethylamino)-4a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-10-fluoro-4,4a,6,11,11a,12,12a,13-octahydro-5-hydroxy-4,6-dioxo-3,7-bis(phenylmethoxy)isoxazolo[5',4';6,7]naphth[2,3-g]isoquinolin-8-yl]-N-[3-(dimethylamino)-2,2-dimethylpropyl]-carbamic acid phenylmethyl ester
CAS No.:1254367-74-2
Molecular Formula:C₅₅H₆₆FN₅O₉Si
Molecular Weight:988.241
Hs Code.:

N-[(4aS,11aR,12aS,13S)-13-(dimethylamino)-4a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-10-fluoro-4,4a,6,11,11a,12,12a,13-octahydro-5-hydroxy-4,6-dioxo-3,7-bis(phenylmethoxy)isoxazolo[5',4';6,7]naphth[2,3-g]isoquinolin-8-yl]-N-[3-(dimethylamino)-2,2-dimethylpropyl]-carbamic acid phenylmethyl ester

Synonyms:N-[(4aS,11aR,12aS,13S)-13-(dimethylamino)-4a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-10-fluoro-4,4a,6,11,11a,12,12a,13-octahydro-5-hydroxy-4,6-dioxo-3,7-bis(phenylmethoxy)isoxazolo[5',4';6,7]naphth[2,3-g]isoquinolin-8-yl]-N-[3-(dimethylamino)-2,2-dimethylpropyl]-carbamic acid phenylmethyl ester

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Chemical Property of N-[(4aS,11aR,12aS,13S)-13-(dimethylamino)-4a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-10-fluoro-4,4a,6,11,11a,12,12a,13-octahydro-5-hydroxy-4,6-dioxo-3,7-bis(phenylmethoxy)isoxazolo[5',4';6,7]naphth[2,3-g]isoquinolin-8-yl]-N-[3-(dimethylamino)-2,2-dimethylpropyl]-carbamic acid phenylmethyl ester

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Technology Process of N-[(4aS,11aR,12aS,13S)-13-(dimethylamino)-4a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-10-fluoro-4,4a,6,11,11a,12,12a,13-octahydro-5-hydroxy-4,6-dioxo-3,7-bis(phenylmethoxy)isoxazolo[5',4';6,7]naphth[2,3-g]isoquinolin-8-yl]-N-[3-(dimethylamino)-2,2-dimethylpropyl]-carbamic acid phenylmethyl ester

There total 14 articles about N-[(4aS,11aR,12aS,13S)-13-(dimethylamino)-4a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-10-fluoro-4,4a,6,11,11a,12,12a,13-octahydro-5-hydroxy-4,6-dioxo-3,7-bis(phenylmethoxy)isoxazolo[5',4';6,7]naphth[2,3-g]isoquinolin-8-yl]-N-[3-(dimethylamino)-2,2-dimethylpropyl]-carbamic acid phenylmethyl ester 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: 26.0%

: 852821-06-8
(4aS,8aS,9S)-3-(benzyloxy)-4a-(tert-butyldimethylsilyloxy)-9-(dimethylamino)-8a,9-dihydronaphtho[2,3-d]isoxazole-4,5(4aH,8H)-dione

: 1254367-73-1
phenyl 3-(benzyloxy)-2-[[(benzyloxy)carbonyl][3-(dimethylamino)-2,2-dimethylpropyl]amino]-6-fluoro-5-methylpyridine-4-carboxylate

: 1254367-74-2
N-[(4aS,11aR,12aS,13S)-13-(dimethylamino)-4a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-10-fluoro-4,4a,6,11,11a,12,12a,13-octahydro-5-hydroxy-4,6-dioxo-3,7-bis(phenylmethoxy)isoxazolo[5',4';6,7]naphth[2,3-g]isoquinolin-8-yl]-N-[3-(dimethylamino)-2,2-dimethylpropyl]-carbamic acid phenylmethyl ester

Guidance literature:: phenyl 3-(benzyloxy)-2-[[(benzyloxy)carbonyl][3-(dimethylamino)-2,2-dimethylpropyl]amino]-6-fluoro-5-methylpyridine-4-carboxylate; With N,N,N,N,-tetramethylethylenediamine; lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.166667h;

(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 - -10 ℃; for 1h;

Reference yield:

: 1254367-44-6
C₂₀H₁₆BrNO₄

: 1254367-74-2
N-[(4aS,11aR,12aS,13S)-13-(dimethylamino)-4a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-10-fluoro-4,4a,6,11,11a,12,12a,13-octahydro-5-hydroxy-4,6-dioxo-3,7-bis(phenylmethoxy)isoxazolo[5',4';6,7]naphth[2,3-g]isoquinolin-8-yl]-N-[3-(dimethylamino)-2,2-dimethylpropyl]-carbamic acid phenylmethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: phosphorus(V) oxybromide / toluene / 0.75 h / 100 °C

2.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tert-butyl carbazate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere

3.1: pyridine; hydrogen fluoride; sodium nitrite / 0 - 20 °C

4.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tetrahydrofuran; 1,4-dioxane / 1.5 h / 70 °C / Inert atmosphere

5.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.08 h / -78 °C

5.2: 0.25 h

6.1: N,N,N,N,-tetramethylethylenediamine; lithium diisopropyl amide / tetrahydrofuran / 0.17 h / -78 °C

6.2: 1 h / -78 - -10 °C

With pyridine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N,N,N,N,-tetramethylethylenediamine; tert-butyl carbazate; hydrogen fluoride; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; lithium hexamethyldisilazane; lithium diisopropyl amide; sodium nitrite; phosphorus(V) oxybromide; In tetrahydrofuran; 1,4-dioxane; toluene;
DOI:10.1021/jm1015389

Reference yield:

: 1254367-40-2
phenyl 3-(benzyloxy)-2,6-dibromo-5-methylisonicotinate

: 1254367-74-2
N-[(4aS,11aR,12aS,13S)-13-(dimethylamino)-4a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-10-fluoro-4,4a,6,11,11a,12,12a,13-octahydro-5-hydroxy-4,6-dioxo-3,7-bis(phenylmethoxy)isoxazolo[5',4';6,7]naphth[2,3-g]isoquinolin-8-yl]-N-[3-(dimethylamino)-2,2-dimethylpropyl]-carbamic acid phenylmethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tert-butyl carbazate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere

2.1: pyridine; hydrogen fluoride; sodium nitrite / 0 - 20 °C

3.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tetrahydrofuran; 1,4-dioxane / 1.5 h / 70 °C / Inert atmosphere

4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.08 h / -78 °C

4.2: 0.25 h

5.1: N,N,N,N,-tetramethylethylenediamine; lithium diisopropyl amide / tetrahydrofuran / 0.17 h / -78 °C

5.2: 1 h / -78 - -10 °C

With pyridine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N,N,N,N,-tetramethylethylenediamine; tert-butyl carbazate; hydrogen fluoride; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; lithium hexamethyldisilazane; lithium diisopropyl amide; sodium nitrite; In tetrahydrofuran; 1,4-dioxane;
DOI:10.1021/jm1015389