(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

Base Information

Chemical Name:(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
CAS No.:896141-39-2
Molecular Formula:C₄₂H₅₅N₃O₉S₂Si
Molecular Weight:838.131
Hs Code.:

(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

Synonyms:(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

Suppliers and Price of (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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (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

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (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

There total 13 articles about (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 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: 59.0%

: 896141-36-9
3-(4-methoxybenzyl)-1-toluenesulfonyl-4-(3-hydroxypropenyl)-1,3-dihydro-imidazol-2-one

: 345642-39-9
(S)-1-(Toluene-4-sulfonyl)-5-triisopropylsilanyloxymethyl-1,5-dihydro-pyrrol-2-one

: 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

Guidance literature:: With 2,6-dimethylpyridine; In benzene; at 114 ℃; for 19h;
DOI:10.1016/j.tet.2005.12.068

Reference yield:

: 17342-08-4
(S)-Pyroglutaminol

: 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

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

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:

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

: 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

Guidance literature:: Multi-step reaction with 6 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

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