(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

Base Information

Chemical Name:(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
CAS No.:1254367-57-1
Molecular Formula:C₄₀H₄₃BrClN₃O₇Si
Molecular Weight:821.24
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 10 articles about (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 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: 84.0%

: 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

: 1254367-42-4
phenyl 3-(benzyloxy)-2-bromo-6-chloro-5-methylisonicotinate

: 1254367-57-1
(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

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 0 ℃; for 1.16667h; Inert atmosphere;

Reference yield:

: 1254367-46-8
C₂₀H₁₆ClNO₄

: 1254367-57-1
(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

Guidance literature:: Multi-step reaction with 2 steps

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

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

With lithium hexamethyldisilazane; phosphorus(V) oxybromide; In tetrahydrofuran; toluene;
DOI:10.1021/jm1015389

Reference yield:

: 1253799-61-9
3-(benzyloxy)-5-chloroisonicotinic acid

: 1254367-57-1
(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

Guidance literature:: Multi-step reaction with 8 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

With dmap; (bis(tricyclohexyl)phosphine)palladium(II) dichloride; anhydrous dipotassium phosphate; oxalyl dichloride; dihydrogen peroxide; triethylamine; N,N-dimethyl-formamide; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; trichlorophosphate; phosphorus(V) oxybromide; In tetrahydrofuran; dichloromethane; water; acetic acid; toluene; 3: Suzuki coupling;
DOI:10.1021/jm1015389