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

Base Information

Chemical Name:(3R,5aS,8aR,8bS)-7-phenyl-3-[(1S)-1-(tert-butyldimethylsiloxy)ethyl]-3,5,5a,6,7,8,8a,8b-octahydro-1H-furo[3,4-e]isoindole-6,8-dione
CAS No.:476212-49-4
Molecular Formula:C₂₄H₃₃NO₄Si
Molecular Weight:427.616
Hs Code.:

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

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

There total 5 articles about (3R,5aS,8aR,8bS)-7-phenyl-3-[(1S)-1-(tert-butyldimethylsiloxy)ethyl]-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%

: 941-69-5
N-phenyl-maleimide

: 476212-39-2
[dimethyl(tert-butyl)siloxy] (1S)-1-[(2R)-3-vinyl-2,5-dihydro-2-furanyl]ethyl ether

: 476212-49-4
(3R,5aS,8aR,8bS)-7-phenyl-3-[(1S)-1-(tert-butyldimethylsiloxy)ethyl]-3,5,5a,6,7,8,8a,8b-octahydro-1H-furo[3,4-e]isoindole-6,8-dione

Guidance literature:: In toluene; at 90 ℃; for 2h;
DOI:10.1016/S0040-4020(02)00548-3

Reference yield:

: 87727-28-4
(S)-2-tert-butyl-dimethyl-silanyloxy propanal

: 476212-49-4
(3R,5aS,8aR,8bS)-7-phenyl-3-[(1S)-1-(tert-butyldimethylsiloxy)ethyl]-3,5,5a,6,7,8,8a,8b-octahydro-1H-furo[3,4-e]isoindole-6,8-dione

Guidance literature:: Multi-step reaction with 5 steps

1: tetrahydrofuran / 4 h / -78 °C

2: 91 percent / Bu₄NF

3: 87 percent / NaH / tetrahydrofuran / 23 °C

4: 92 percent / ethylene / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 5 h / 23 °C / 760 Torr

5: 93 percent / toluene / 2 h / 90 °C

With ethene; tetrabutyl ammonium fluoride; sodium hydride; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; toluene; 5: Diels-Alder reaction;
DOI:10.1016/S0040-4020(02)00548-3

Reference yield:

: 127488-34-0
(3R,4S)-4-((tert-butyldimethylsilyl)oxy)pent-1-yn-3-ol

: 476212-49-4
(3R,5aS,8aR,8bS)-7-phenyl-3-[(1S)-1-(tert-butyldimethylsiloxy)ethyl]-3,5,5a,6,7,8,8a,8b-octahydro-1H-furo[3,4-e]isoindole-6,8-dione

Guidance literature:: Multi-step reaction with 3 steps

1: 87 percent / NaH / tetrahydrofuran / 23 °C

2: 92 percent / ethylene / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 5 h / 23 °C / 760 Torr

3: 93 percent / toluene / 2 h / 90 °C

With ethene; sodium hydride; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; toluene; 3: Diels-Alder reaction;
DOI:10.1016/S0040-4020(02)00548-3