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

Base Information

• Chemical Name: N-[(4aS,11aR,12aS,13S)-10-chloro-13-(dimethylamino)-4a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11a,12,12a,13-tetrahydro-5-hydroxy-3,7-bis(phenylmethoxy)-isoxazolo[5',4':6,7]naphth[2,3-g]-isoquinolin-8-yl]-carbamic acid 1,1-dimethylethyl ester
• CAS No.: 1254367-59-3
• Molecular Formula: C₄₅H₅₃ClN₄O₉Si
• Molecular Weight: 857.476

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

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

Chemical Property:

Purity/Quality:

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

There total 10 articles about N-[(4aS,11aR,12aS,13S)-10-chloro-13-(dimethylamino)-4a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11a,12,12a,13-tetrahydro-5-hydroxy-3,7-bis(phenylmethoxy)-isoxazolo[5',4':6,7]naphth[2,3-g]-isoquinolin-8-yl]-carbamic acid 1,1-dimethylethyl 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: 40.0%

tert-butyl carbazate (4248-19-5) + (4aS,11aR,12aS,13S)-8-bromo-10-chloro-13-(dimethylamino)-4a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11a,12,12a,13-tetrahydro-5-hydroxy-3,7-bis(phenylmethoxy)-isoxazolo[5',4':6,7]naphth[2,3-g]-isoquinoline-4,6(4aH,11H)-dione (1254367-57-1) → N-[(4aS,11aR,12aS,13S)-10-chloro-13-(dimethylamino)-4a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11a,12,12a,13-tetrahydro-5-hydroxy-3,7-bis(phenylmethoxy)-isoxazolo[5',4':6,7]naphth[2,3-g]-isoquinolin-8-yl]-carbamic acid 1,1-dimethylethyl ester (1254367-59-3)

Guidance literature:

With potassium phosphate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In 1,4-dioxane; at 100 ℃; for 2h;

Reference yield:

C20H16ClNO4 (1254367-46-8) → N-[(4aS,11aR,12aS,13S)-10-chloro-13-(dimethylamino)-4a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11a,12,12a,13-tetrahydro-5-hydroxy-3,7-bis(phenylmethoxy)-isoxazolo[5',4':6,7]naphth[2,3-g]-isoquinolin-8-yl]-carbamic acid 1,1-dimethylethyl ester (1254367-59-3)

Guidance literature:

Multi-step reaction with 3 steps

1: phosphorus(V) oxybromide / toluene / 1 h / 80 °C

2: lithium hexamethyldisilazane / tetrahydrofuran / 1.17 h / -78 - 0 °C

3: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; anhydrous dipotassium phosphate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 2 h / 100 °C / Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; anhydrous dipotassium phosphate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; lithium hexamethyldisilazane; phosphorus(V) oxybromide; In tetrahydrofuran; 1,4-dioxane; toluene;

DOI:10.1021/jm1015389

Reference yield:

3-(benzyloxy)-5-chloroisonicotinic acid (1253799-61-9) → N-[(4aS,11aR,12aS,13S)-10-chloro-13-(dimethylamino)-4a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11a,12,12a,13-tetrahydro-5-hydroxy-3,7-bis(phenylmethoxy)-isoxazolo[5',4':6,7]naphth[2,3-g]-isoquinolin-8-yl]-carbamic acid 1,1-dimethylethyl ester (1254367-59-3)

Guidance literature:

Multi-step reaction with 9 steps

1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane

2: dmap; triethylamine / dichloromethane / 1 h

3: (bis(tricyclohexyl)phosphine)palladium(II) dichloride; anhydrous dipotassium phosphate / water; toluene / 16 h / 100 °C

4: dihydrogen peroxide / water; acetic acid / 6 h / 80 °C

5: trichlorophosphate / toluene / 2 h / 100 °C

6: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C

7: phosphorus(V) oxybromide / toluene / 1 h / 80 °C

8: lithium hexamethyldisilazane / tetrahydrofuran / 1.17 h / -78 - 0 °C

9: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; anhydrous dipotassium phosphate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 2 h / 100 °C / Inert atmosphere

With dmap; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (bis(tricyclohexyl)phosphine)palladium(II) dichloride; anhydrous dipotassium phosphate; oxalyl dichloride; dihydrogen peroxide; triethylamine; N,N-dimethyl-formamide; 3-chloro-benzenecarboperoxoic acid; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; lithium hexamethyldisilazane; trichlorophosphate; phosphorus(V) oxybromide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetic acid; toluene; 3: Suzuki coupling;

DOI:10.1021/jm1015389

upstream raw materials:

tert-butyl carbazate

(4aS,11aR,12aS,13S)-8-bromo-10-chloro-13-(dimethylamino)-4a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11a,12,12a,13-tetrahydro-5-hydroxy-3,7-bis(phenylmethoxy)-isoxazolo[5',4':6,7]naphth[2,3-g]-isoquinoline-4,6(4aH,11H)-dione

C₂₀H₁₆ClNO₄

3-(benzyloxy)-5-chloroisonicotinic acid

Downstream raw materials:

C₄₀H₄₅ClN₄O₇Si

C₄₂H₄₆BrClN₄O₈Si

N-[(4aS,11aR,12aS,13S)-10-chloro-13-(dimethylamino)-4a-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4,4a,6,11,11a,12,12a,13-octahydro-5-hydroxy-4,6-dioxo-3,7-bis(phenylmethoxy)isoxazolo[50,40:6,7]naphth[2,3-g]isoquinolin-8-yl]-2-[(1,1-dimethylethyl)amino]-acetamide

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