5-(tert-butyl-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-benzyl)-7-(toluene-4-sulfonyl)-1-[2-(toluene-4-sulfonyl)-ethyl]-8-triisopropylsilanyloxymethyl-1,3,4,5,5a,7,8,8a-octahydro-imidazo[4,5-e]isoindole-2,6-dione

Base Information

Chemical Name:5-(tert-butyl-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-benzyl)-7-(toluene-4-sulfonyl)-1-[2-(toluene-4-sulfonyl)-ethyl]-8-triisopropylsilanyloxymethyl-1,3,4,5,5a,7,8,8a-octahydro-imidazo[4,5-e]isoindole-2,6-dione
CAS No.:852615-10-2
Molecular Formula:C₆₁H₇₉N₃O₁₀S₂Si₂
Molecular Weight:1134.62
Hs Code.:

5-(tert-butyl-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-benzyl)-7-(toluene-4-sulfonyl)-1-[2-(toluene-4-sulfonyl)-ethyl]-8-triisopropylsilanyloxymethyl-1,3,4,5,5a,7,8,8a-octahydro-imidazo[4,5-e]isoindole-2,6-dione

Synonyms:5-(tert-butyl-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-benzyl)-7-(toluene-4-sulfonyl)-1-[2-(toluene-4-sulfonyl)-ethyl]-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 5-(tert-butyl-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-benzyl)-7-(toluene-4-sulfonyl)-1-[2-(toluene-4-sulfonyl)-ethyl]-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 5-(tert-butyl-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-benzyl)-7-(toluene-4-sulfonyl)-1-[2-(toluene-4-sulfonyl)-ethyl]-8-triisopropylsilanyloxymethyl-1,3,4,5,5a,7,8,8a-octahydro-imidazo[4,5-e]isoindole-2,6-dione

There total 32 articles about 5-(tert-butyl-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-benzyl)-7-(toluene-4-sulfonyl)-1-[2-(toluene-4-sulfonyl)-ethyl]-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%

: 5-(tert-butyl-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-benzyl)-7-(toluene-4-sulfonyl)-1-[2-(toluene-4-sulfonyl)vinyl]-8-triisopropylsilanyloxymethyl-1,3,4,5,5a,7,8,8a-octahydro-imidazo[4,5-e]isoindole-2,6-dione

: 852615-10-2
5-(tert-butyl-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-benzyl)-7-(toluene-4-sulfonyl)-1-[2-(toluene-4-sulfonyl)-ethyl]-8-triisopropylsilanyloxymethyl-1,3,4,5,5a,7,8,8a-octahydro-imidazo[4,5-e]isoindole-2,6-dione

Guidance literature:: With hydrogen; palladium dihydroxide; In ethyl acetate; at 25 ℃; for 24h;
DOI:10.1021/ol0473602

Reference yield:

: 17342-08-4
(S)-Pyroglutaminol

: 852615-10-2
5-(tert-butyl-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-benzyl)-7-(toluene-4-sulfonyl)-1-[2-(toluene-4-sulfonyl)-ethyl]-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

1.1: 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: 2,6-lutidine / benzene / 1 h / 160 °C / microwave irradiation

4.2: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂

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

Reference yield:

: 3-(3,4-dimethoxybenzyl)-2-oxo-1-[2-(toluene-4-sulfonyl)-vinyl]-2,3-dihydro-1H-imidazole-4-carboxylic acid methyl ester

: 852615-10-2
5-(tert-butyl-diphenyl-silanyloxymethyl)-3-(3,4-dimethoxy-benzyl)-7-(toluene-4-sulfonyl)-1-[2-(toluene-4-sulfonyl)-ethyl]-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: DIBAl-H

2.1: activated manganese dioxide / CH₂Cl₂

3.1: NaH / tetrahydrofuran / 0 - 25 °C

3.2: tetrahydrofuran / 2 h

4.1: DIBAl-H / CH₂Cl₂ / -78 °C

5.1: 2,6-lutidine / benzene / 1 h / 160 °C / microwave irradiation

5.2: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂

With 2,6-dimethylpyridine; manganese(IV) oxide; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; benzene; 3.2: Horner-Wadsworth-Emmons reaction / 5.1: Diels-Alder reaction;
DOI:10.1016/j.tet.2005.12.068