(3aS,4R,7aS)-6-(tert-butyldimethylsilyloxy)-3a,4,7,7a-tetrahydro-2-phenyl-4-[(R)-4-phenyl-2-oxazolidinon-3-yl]-1H-isoindole-1,3-(2H)-dione

Base Information

Chemical Name:(3aS,4R,7aS)-6-(tert-butyldimethylsilyloxy)-3a,4,7,7a-tetrahydro-2-phenyl-4-[(R)-4-phenyl-2-oxazolidinon-3-yl]-1H-isoindole-1,3-(2H)-dione
CAS No.:325479-39-8
Molecular Formula:C₂₉H₃₄N₂O₅Si
Molecular Weight:518.685
Hs Code.:

Synonyms:(3aS,4R,7aS)-6-(tert-butyldimethylsilyloxy)-3a,4,7,7a-tetrahydro-2-phenyl-4-[(R)-4-phenyl-2-oxazolidinon-3-yl]-1H-isoindole-1,3-(2H)-dione

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Chemical Property of (3aS,4R,7aS)-6-(tert-butyldimethylsilyloxy)-3a,4,7,7a-tetrahydro-2-phenyl-4-[(R)-4-phenyl-2-oxazolidinon-3-yl]-1H-isoindole-1,3-(2H)-dione

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Technology Process of (3aS,4R,7aS)-6-(tert-butyldimethylsilyloxy)-3a,4,7,7a-tetrahydro-2-phenyl-4-[(R)-4-phenyl-2-oxazolidinon-3-yl]-1H-isoindole-1,3-(2H)-dione

There total 5 articles about (3aS,4R,7aS)-6-(tert-butyldimethylsilyloxy)-3a,4,7,7a-tetrahydro-2-phenyl-4-[(R)-4-phenyl-2-oxazolidinon-3-yl]-1H-isoindole-1,3-(2H)-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: 100.0%

: 941-69-5
N-phenyl-maleimide

: 325479-30-9
(R,E)-3-(tert-butyldimethylsiloxy)-1-(4-phenyl-2-oxazolidinon-3-yl)-1,3-butadiene

: 325479-39-8
(3aS,4R,7aS)-6-(tert-butyldimethylsilyloxy)-3a,4,7,7a-tetrahydro-2-phenyl-4-[(R)-4-phenyl-2-oxazolidinon-3-yl]-1H-isoindole-1,3-(2H)-dione

Guidance literature:: In toluene; at -45 - 20 ℃; for 24h;
DOI:10.1021/jo005619y

Reference yield:

: 875-74-1
(R)-phenylglycine

: 325479-39-8
(3aS,4R,7aS)-6-(tert-butyldimethylsilyloxy)-3a,4,7,7a-tetrahydro-2-phenyl-4-[(R)-4-phenyl-2-oxazolidinon-3-yl]-1H-isoindole-1,3-(2H)-dione

Guidance literature:: Multi-step reaction with 5 steps

1.1: 93 percent / LiBH₄; trimethylsilyl chloride / tetrahydrofuran / 49 h / 0 - 20 °C

2.1: 90 percent / K₂CO₃ / 2.5 h / 130 °C

3.1: 88 percent / N-methylmorpholine / CH₂Cl₂ / 16 h / 20 °C

4.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

4.2: 76 percent / tetrahydrofuran / -78 - 20 °C

5.1: 100 percent / toluene / 24 h / -45 - 20 °C

With 4-methyl-morpholine; lithium borohydride; chloro-trimethyl-silane; sodium hexamethyldisilazane; potassium carbonate; In tetrahydrofuran; dichloromethane; toluene; 5.1: Diels-Alder reaction;
DOI:10.1021/jo005619y

Reference yield:

: 56613-80-0
D-2-phenylglycinol

: 325479-39-8
(3aS,4R,7aS)-6-(tert-butyldimethylsilyloxy)-3a,4,7,7a-tetrahydro-2-phenyl-4-[(R)-4-phenyl-2-oxazolidinon-3-yl]-1H-isoindole-1,3-(2H)-dione

Guidance literature:: Multi-step reaction with 4 steps

1.1: 90 percent / K₂CO₃ / 2.5 h / 130 °C

2.1: 88 percent / N-methylmorpholine / CH₂Cl₂ / 16 h / 20 °C

3.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

3.2: 76 percent / tetrahydrofuran / -78 - 20 °C

4.1: 100 percent / toluene / 24 h / -45 - 20 °C

With 4-methyl-morpholine; sodium hexamethyldisilazane; potassium carbonate; In tetrahydrofuran; dichloromethane; toluene; 4.1: Diels-Alder reaction;
DOI:10.1021/jo005619y