(3S,5aR,8aS,8bR)-3-[1-(benzyloxy)ethyl]-7-phenyl-3,5,5a,6,7,8,8a,8b-octahydro-1H-furo[3,4-e]isoindole-6,8-dione

Base Information

• Chemical Name: (3S,5aR,8aS,8bR)-3-[1-(benzyloxy)ethyl]-7-phenyl-3,5,5a,6,7,8,8a,8b-octahydro-1H-furo[3,4-e]isoindole-6,8-dione
• CAS No.: 344285-66-1
• Molecular Formula: C₂₅H₂₅NO₄
• Molecular Weight: 403.478

Synonyms:(3S,5aR,8aS,8bR)-3-[1-(benzyloxy)ethyl]-7-phenyl-3,5,5a,6,7,8,8a,8b-octahydro-1H-furo[3,4-e]isoindole-6,8-dione

Chemical Property of (3S,5aR,8aS,8bR)-3-[1-(benzyloxy)ethyl]-7-phenyl-3,5,5a,6,7,8,8a,8b-octahydro-1H-furo[3,4-e]isoindole-6,8-dione

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Technology Process of (3S,5aR,8aS,8bR)-3-[1-(benzyloxy)ethyl]-7-phenyl-3,5,5a,6,7,8,8a,8b-octahydro-1H-furo[3,4-e]isoindole-6,8-dione

There total 2 articles about (3S,5aR,8aS,8bR)-3-[1-(benzyloxy)ethyl]-7-phenyl-3,5,5a,6,7,8,8a,8b-octahydro-1H-furo[3,4-e]isoindole-6,8-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%

N-phenyl-maleimide (941-69-5) + (2S)-2-[(1S)-1-(benzyloxy)ethyl]-3-vinyl-2,5-dihydrofuran (344285-57-0) → (3S,5aR,8aS,8bR)-3-[1-(benzyloxy)ethyl]-7-phenyl-3,5,5a,6,7,8,8a,8b-octahydro-1H-furo[3,4-e]isoindole-6,8-dione (344285-66-1)

Guidance literature:

In toluene; at 80 ℃; for 3h;

DOI:10.1021/ol015622j

Reference yield:

(S)-2-(benzyloxy)propanal (81445-44-5) → (3S,5aR,8aS,8bR)-3-[1-(benzyloxy)ethyl]-7-phenyl-3,5,5a,6,7,8,8a,8b-octahydro-1H-furo[3,4-e]isoindole-6,8-dione (344285-66-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: TiCl₄ / CH₂Cl₂ / 1 h / -78 °C

1.2: 87 mg / m-CPBA / CH₂Cl₂ / 8 h

2.1: 93 percent / toluene / 3 h / 80 °C

With titanium tetrachloride; In dichloromethane; toluene; 2.1: Diels-Alder reaction;

DOI:10.1021/ol015622j

Reference yield:

(3S,5aR,8aS,8bR)-3-[1-(benzyloxy)ethyl]-7-phenyl-3,5,5a,6,7,8,8a,8b-octahydro-1H-furo[3,4-e]isoindole-6,8-dione (344285-66-1) → (3S,3aS,5aR,8aS,8bS)-3-((S)-1-Hydroxy-ethyl)-7-phenyl-octahydro-furo[3,4-e]isoindole-6,8-dione

Guidance literature:

With hydrogen; palladium;

DOI:10.1021/ol015622j

upstream raw materials:

N-phenyl-maleimide

(2S)-2-[(1S)-1-(benzyloxy)ethyl]-3-vinyl-2,5-dihydrofuran

(S)-2-(benzyloxy)propanal

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