(5R,5aS,8S,8aS)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(4-methoxy-benzyl)-1,7-bis-(toluene-4-sulfonyl)-8-triisopropylsilanyloxymethyl-1,3,4,5,5a,7,8,8a-octahydro-imidazo[4,5-e]isoindole-2,6-dione

Base Information

Chemical Name:(5R,5aS,8S,8aS)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(4-methoxy-benzyl)-1,7-bis-(toluene-4-sulfonyl)-8-triisopropylsilanyloxymethyl-1,3,4,5,5a,7,8,8a-octahydro-imidazo[4,5-e]isoindole-2,6-dione
CAS No.:896140-95-7
Molecular Formula:C₄₈H₆₉N₃O₉S₂Si₂
Molecular Weight:952.394
Hs Code.:

(5R,5aS,8S,8aS)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(4-methoxy-benzyl)-1,7-bis-(toluene-4-sulfonyl)-8-triisopropylsilanyloxymethyl-1,3,4,5,5a,7,8,8a-octahydro-imidazo[4,5-e]isoindole-2,6-dione

Synonyms:(5R,5aS,8S,8aS)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(4-methoxy-benzyl)-1,7-bis-(toluene-4-sulfonyl)-8-triisopropylsilanyloxymethyl-1,3,4,5,5a,7,8,8a-octahydro-imidazo[4,5-e]isoindole-2,6-dione

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Chemical Property of (5R,5aS,8S,8aS)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(4-methoxy-benzyl)-1,7-bis-(toluene-4-sulfonyl)-8-triisopropylsilanyloxymethyl-1,3,4,5,5a,7,8,8a-octahydro-imidazo[4,5-e]isoindole-2,6-dione

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Technology Process of (5R,5aS,8S,8aS)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(4-methoxy-benzyl)-1,7-bis-(toluene-4-sulfonyl)-8-triisopropylsilanyloxymethyl-1,3,4,5,5a,7,8,8a-octahydro-imidazo[4,5-e]isoindole-2,6-dione

There total 14 articles about (5R,5aS,8S,8aS)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(4-methoxy-benzyl)-1,7-bis-(toluene-4-sulfonyl)-8-triisopropylsilanyloxymethyl-1,3,4,5,5a,7,8,8a-octahydro-imidazo[4,5-e]isoindole-2,6-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: 92.0%

: 896141-39-2
(5R,5aS,8S,8aS)-5-Hydroxymethyl-3-(4-methoxy-benzyl)-1,7-bis-(toluene-4-sulfonyl)-8-triisopropylsilanyloxymethyl-1,3,4,5,5a,7,8,8a-octahydro-imidazo[4,5-e]isoindole-2,6-dione

: 18162-48-6
tert-butyldimethylsilyl chloride

: 896140-95-7
(5R,5aS,8S,8aS)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(4-methoxy-benzyl)-1,7-bis-(toluene-4-sulfonyl)-8-triisopropylsilanyloxymethyl-1,3,4,5,5a,7,8,8a-octahydro-imidazo[4,5-e]isoindole-2,6-dione

Guidance literature:: With dmap; triethylamine; In dichloromethane;
DOI:10.1016/j.tet.2005.12.068

Reference yield:

: 17342-08-4
(S)-Pyroglutaminol

: 896140-95-7
(5R,5aS,8S,8aS)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(4-methoxy-benzyl)-1,7-bis-(toluene-4-sulfonyl)-8-triisopropylsilanyloxymethyl-1,3,4,5,5a,7,8,8a-octahydro-imidazo[4,5-e]isoindole-2,6-dione

Guidance literature:: Multi-step reaction with 5 steps

1.1: 66 percent / imidazole / dimethylformamide

2.1: 90 percent / NaHMDS / tetrahydrofuran

3.1: LiHMDS / tetrahydrofuran / -78 °C

3.2: tetrahydrofuran / -78 °C

3.3: 74 percent / H₂O₂ / ethyl acetate / 0 °C

4.1: 59 percent / 2,6-lutidine / benzene / 19 h / 114 °C

5.1: 92 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂

With 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium hexamethyldisilazane; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; benzene; 4.1: Diels-Alder reaction;
DOI:10.1016/j.tet.2005.12.068

Reference yield:

: 852615-13-5
1-(p-toluenesulfonyl)-4-(methoxycarbonyl)-2,3-dihydro-1H-imidazol-2-one

: 896140-95-7
(5R,5aS,8S,8aS)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(4-methoxy-benzyl)-1,7-bis-(toluene-4-sulfonyl)-8-triisopropylsilanyloxymethyl-1,3,4,5,5a,7,8,8a-octahydro-imidazo[4,5-e]isoindole-2,6-dione

Guidance literature:: Multi-step reaction with 7 steps

1.1: 83 percent / K₂CO₃ / acetonitrile / 70 °C

2.1: DIBAl-H / CH₂Cl₂ / -78 °C

3.1: activated manganese dioxide / CH₂Cl₂

4.1: NaH / tetrahydrofuran / 0 - 25 °C

4.2: tetrahydrofuran

5.1: DIBAl-H / CH₂Cl₂ / -78 °C

6.1: 59 percent / 2,6-lutidine / benzene / 19 h / 114 °C

7.1: 92 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂

With 2,6-dimethylpyridine; dmap; manganese(IV) oxide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; acetonitrile; benzene; 4.2: Horner-Wadsworth-Emmons reaction / 6.1: Diels-Alder reaction;
DOI:10.1016/j.tet.2005.12.068