(5R,5aS,8S,8aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-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-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-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.:852615-27-1
Molecular Formula:C₅₉H₇₅N₃O₁₀S₂Si₂
Molecular Weight:1106.56
Hs Code.:

(5R,5aS,8S,8aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-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-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-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-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-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-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-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 5 articles about (5R,5aS,8S,8aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-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: 93.0%

: 852615-00-0
3-(3,4-dimethoxybenzyl)-5-hydroxymethyl-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

: 58479-61-1
tert-butylchlorodiphenylsilane

: 852615-27-1
(5R,5aS,8S,8aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-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:10.1021/ol0473602

Reference yield:

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

: 852615-27-1
(5R,5aS,8S,8aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-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 8 steps

1.1: 95 percent / K₂CO₃ / dimethylformamide / 20 h / 60 °C

2.1: 80 percent / DIBAL-H / CH₂Cl₂ / 0.5 h / -78 °C

3.1: 86 percent / MnO₂ / CH₂Cl₂ / 10 h / 20 °C

4.1: NaH / tetrahydrofuran / 0 - 22 °C

4.2: 84 percent / tetrahydrofuran / 1 h / 20 °C

5.1: 99 percent / DIBAL-H / CH₂Cl₂ / 2 h

6.1: 2,6-lutidine / phenol / 48 h / 95 °C

7.1: 2,6-lutidine / phenol / 48 h / 114 °C

8.1: 93 percent / Et₃N; DMAP / CH₂Cl₂

With 2,6-dimethylpyridine; dmap; manganese(IV) oxide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; phenol; 4.2: Horner-Wadsworth olefination / 6.1: Diels-Alder reaction;
DOI:10.1021/ol0473602

Reference yield:

: 896141-35-8
3-(3,4-dimethoxybenzyl)-1-toluenesulfonyl-4-(ehtylpropenoate)-2,3-dihydro-1H-imidazol-2-one

: 852615-27-1
(5R,5aS,8S,8aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-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 4 steps

1: 99 percent / DIBAL-H / CH₂Cl₂ / 2 h

2: 2,6-lutidine / phenol / 48 h / 95 °C

3: 2,6-lutidine / phenol / 48 h / 114 °C

4: 93 percent / Et₃N; DMAP / CH₂Cl₂

With 2,6-dimethylpyridine; dmap; diisobutylaluminium hydride; triethylamine; In dichloromethane; phenol; 2: Diels-Alder reaction;
DOI:10.1021/ol0473602