(5R,5aS,8S,8aS)-5-Hydroxymethyl-3-(4-methoxy-benzyl)-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)-8-triisopropylsilanyloxymethyl-1,3,4,5,5a,7,8,8a-octahydro-imidazo[4,5-e]isoindole-2,6-dione
CAS No.:896140-99-1
Molecular Formula:C₂₈H₄₃N₃O₅Si
Molecular Weight:529.752
Hs Code.:

(5R,5aS,8S,8aS)-5-Hydroxymethyl-3-(4-methoxy-benzyl)-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)-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-Hydroxymethyl-3-(4-methoxy-benzyl)-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-Hydroxymethyl-3-(4-methoxy-benzyl)-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)-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: 87.0%

: 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

: 896140-99-1
(5R,5aS,8S,8aS)-5-Hydroxymethyl-3-(4-methoxy-benzyl)-8-triisopropylsilanyloxymethyl-1,3,4,5,5a,7,8,8a-octahydro-imidazo[4,5-e]isoindole-2,6-dione

Guidance literature:: With sodium naphthalenide; In tetrahydrofuran; at -78 ℃;
DOI:10.1016/j.tet.2005.12.068

Reference yield:

: 17342-08-4
(S)-Pyroglutaminol

: 896140-99-1
(5R,5aS,8S,8aS)-5-Hydroxymethyl-3-(4-methoxy-benzyl)-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: 87 percent / sodium naphthalenide / tetrahydrofuran / -78 °C

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

Reference yield:

: 896141-33-6
3-(4-methoxybenzyl)-1-(toluene-4-sulfonyl)-4-formyl-2,3-dihydro-1H-imidazol-2-one

: 896140-99-1
(5R,5aS,8S,8aS)-5-Hydroxymethyl-3-(4-methoxy-benzyl)-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: NaH / tetrahydrofuran / 0 - 25 °C

1.2: tetrahydrofuran

2.1: DIBAl-H / CH₂Cl₂ / -78 °C

3.1: 59 percent / 2,6-lutidine / benzene / 19 h / 114 °C

4.1: 87 percent / sodium naphthalenide / tetrahydrofuran / -78 °C

With 2,6-dimethylpyridine; sodium naphthalenide; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; benzene; 1.2: Horner-Wadsworth-Emmons reaction / 3.1: Diels-Alder reaction;
DOI:10.1016/j.tet.2005.12.068