4-(tert-butyldimethylsiloxy)-2-(3,4-dimethoxybenzyl)-6-methoxy-5-{[(4a'S,5'S,8a'S)-5',8a'-dimethyl-6'-oxooctahydro-2'H-spiro[[1,3]dioxolane-2,1'-naphthalene]-5'-yl]methyl}-isoindolin-1-one

Base Information

Chemical Name:4-(tert-butyldimethylsiloxy)-2-(3,4-dimethoxybenzyl)-6-methoxy-5-{[(4a'S,5'S,8a'S)-5',8a'-dimethyl-6'-oxooctahydro-2'H-spiro[[1,3]dioxolane-2,1'-naphthalene]-5'-yl]methyl}-isoindolin-1-one
CAS No.:1236125-70-4
Molecular Formula:C₃₉H₅₅NO₈Si
Molecular Weight:693.953
Hs Code.:

4-(tert-butyldimethylsiloxy)-2-(3,4-dimethoxybenzyl)-6-methoxy-5-{[(4a'S,5'S,8a'S)-5',8a'-dimethyl-6'-oxooctahydro-2'H-spiro[[1,3]dioxolane-2,1'-naphthalene]-5'-yl]methyl}-isoindolin-1-one

Synonyms:4-(tert-butyldimethylsiloxy)-2-(3,4-dimethoxybenzyl)-6-methoxy-5-{[(4a'S,5'S,8a'S)-5',8a'-dimethyl-6'-oxooctahydro-2'H-spiro[[1,3]dioxolane-2,1'-naphthalene]-5'-yl]methyl}-isoindolin-1-one

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Chemical Property of 4-(tert-butyldimethylsiloxy)-2-(3,4-dimethoxybenzyl)-6-methoxy-5-{[(4a'S,5'S,8a'S)-5',8a'-dimethyl-6'-oxooctahydro-2'H-spiro[[1,3]dioxolane-2,1'-naphthalene]-5'-yl]methyl}-isoindolin-1-one

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Technology Process of 4-(tert-butyldimethylsiloxy)-2-(3,4-dimethoxybenzyl)-6-methoxy-5-{[(4a'S,5'S,8a'S)-5',8a'-dimethyl-6'-oxooctahydro-2'H-spiro[[1,3]dioxolane-2,1'-naphthalene]-5'-yl]methyl}-isoindolin-1-one

There total 15 articles about 4-(tert-butyldimethylsiloxy)-2-(3,4-dimethoxybenzyl)-6-methoxy-5-{[(4a'S,5'S,8a'S)-5',8a'-dimethyl-6'-oxooctahydro-2'H-spiro[[1,3]dioxolane-2,1'-naphthalene]-5'-yl]methyl}-isoindolin-1-one 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: 76.0%

: 26742-33-6
(4aS)-1,4aβ-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione-5-ethyeneacetal

: 1236125-34-0
5-bromomethyl-4-(tert-butyldimethylsiloxy)-2-(3,4-dimethoxybenzyl)-6-methoxyisoindolin-1-one

: 1236125-70-4
4-(tert-butyldimethylsiloxy)-2-(3,4-dimethoxybenzyl)-6-methoxy-5-{[(4a'S,5'S,8a'S)-5',8a'-dimethyl-6'-oxooctahydro-2'H-spiro[[1,3]dioxolane-2,1'-naphthalene]-5'-yl]methyl}-isoindolin-1-one

Guidance literature:: (4aS)-1,4aβ-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione-5-ethyeneacetal; With ammonia; lithium; In tetrahydrofuran; at -78 - -30 ℃; Inert atmosphere;

5-bromomethyl-4-(tert-butyldimethylsiloxy)-2-(3,4-dimethoxybenzyl)-6-methoxyisoindolin-1-one; In tetrahydrofuran; at -30 - 20 ℃;
DOI:10.1039/c000193g

Reference yield:

: 1310461-17-6
methyl 8-aminomethyl-5-methoxy-2,2-dimethyl-4H-benzo[d][1,3]dioxine-7carboxylate hydrochloride salt

: 1236125-70-4
4-(tert-butyldimethylsiloxy)-2-(3,4-dimethoxybenzyl)-6-methoxy-5-{[(4a'S,5'S,8a'S)-5',8a'-dimethyl-6'-oxooctahydro-2'H-spiro[[1,3]dioxolane-2,1'-naphthalene]-5'-yl]methyl}-isoindolin-1-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium methylate / methanol / 1 h / 20 °C

2.1: sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

3.1: hydrogenchloride / tetrahydrofuran; water / 20 °C

4.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C

5.1: hydrogen fluoride / water; acetonitrile / 0 °C

6.1: carbon tetrabromide; triphenylphosphine / dichloromethane

7.1: lithium / tetrahydrofuran; ammonia / -78 - -30 °C / Inert atmosphere; liquid NH₃

7.2: -78 - -30 °C / Inert atmosphere

7.3: -30 - 20 °C / Inert atmosphere

With 1H-imidazole; hydrogenchloride; carbon tetrabromide; hydrogen fluoride; sodium methylate; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; lithium; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; ammonia; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/ejoc.201100173

Reference yield:

: 1236125-62-4
5-methoxy-2,2-dimethyl-8,9-dihydro-[1,3]dioxino[4,5-e]isoindol-7(4H)-one

: 1236125-70-4
4-(tert-butyldimethylsiloxy)-2-(3,4-dimethoxybenzyl)-6-methoxy-5-{[(4a'S,5'S,8a'S)-5',8a'-dimethyl-6'-oxooctahydro-2'H-spiro[[1,3]dioxolane-2,1'-naphthalene]-5'-yl]methyl}-isoindolin-1-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2.1: hydrogenchloride / tetrahydrofuran; water / 20 °C

3.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C

4.1: hydrogen fluoride / water; acetonitrile / 0 °C

5.1: carbon tetrabromide; triphenylphosphine / dichloromethane

6.1: lithium / tetrahydrofuran; ammonia / -78 - -30 °C / Inert atmosphere; liquid NH₃

6.2: -78 - -30 °C / Inert atmosphere

6.3: -30 - 20 °C / Inert atmosphere

With 1H-imidazole; hydrogenchloride; carbon tetrabromide; hydrogen fluoride; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; lithium; triphenylphosphine; In tetrahydrofuran; dichloromethane; ammonia; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/ejoc.201100173