(3S,5S)-5-(4-(benzyloxy)benzyl)-3-hydroxy-1,3-dimethylpyrrolidine-2,4-dione

Base Information

Chemical Name:(3S,5S)-5-(4-(benzyloxy)benzyl)-3-hydroxy-1,3-dimethylpyrrolidine-2,4-dione
CAS No.:1370332-13-0
Molecular Formula:C₂₀H₂₁NO₄
Molecular Weight:339.391
Hs Code.:

Synonyms:(3S,5S)-5-(4-(benzyloxy)benzyl)-3-hydroxy-1,3-dimethylpyrrolidine-2,4-dione

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Chemical Property of (3S,5S)-5-(4-(benzyloxy)benzyl)-3-hydroxy-1,3-dimethylpyrrolidine-2,4-dione

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Technology Process of (3S,5S)-5-(4-(benzyloxy)benzyl)-3-hydroxy-1,3-dimethylpyrrolidine-2,4-dione

There total 7 articles about (3S,5S)-5-(4-(benzyloxy)benzyl)-3-hydroxy-1,3-dimethylpyrrolidine-2,4-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: 76.0%

: C₂₀H₂₃NO₃

: 1370332-13-0
(3S,5S)-5-(4-(benzyloxy)benzyl)-3-hydroxy-1,3-dimethylpyrrolidine-2,4-dione

Guidance literature:: With Dess-Martin periodane; In dimethyl sulfoxide; at 55 ℃; for 12h; diastereoselective reaction;
DOI:10.1002/asia.201100809

Reference yield: 68.0%

: (S)-5-(4-(benzyloxy)benzyl)-4-(tert-butyldiphenylsilyloxy)-1,3-dimethyl-1H-pyrrol-2(5H)-one

: 1370332-13-0
(3S,5S)-5-(4-(benzyloxy)benzyl)-3-hydroxy-1,3-dimethylpyrrolidine-2,4-dione

: (3R,5S)-5-(4-(benzyloxy)benzyl)-3-hydroxy-1,3-dimethylpyrrolidine-2,4-dione

Guidance literature:: (S)-5-(4-(benzyloxy)benzyl)-4-(tert-butyldiphenylsilyloxy)-1,3-dimethyl-1H-pyrrol-2(5H)-one; With potassium fluoride; oxygen; In acetonitrile; at 20 ℃; for 1h;

With sodium thiosulfate; In water; acetonitrile; for 48h; Overall yield = 80 %; diastereoselective reaction;
DOI:10.1039/c6ob01836j

Reference yield:

: 64263-81-6
N-(tert-butyloxycarbonyl)-N-methyl-O-(phenylmethyl)-L-tyrosine

: 1370332-13-0
(3S,5S)-5-(4-(benzyloxy)benzyl)-3-hydroxy-1,3-dimethylpyrrolidine-2,4-dione

: (3R,5S)-5-(4-(benzyloxy)benzyl)-3-hydroxy-1,3-dimethylpyrrolidine-2,4-dione

Guidance literature:: Multi-step reaction with 5 steps

1.1: thionyl chloride / 48 h / 20 °C / Cooling with ice

2.1: triethylamine / dichloromethane / 2 h / 20 °C

3.1: lithium telluride; lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 20 °C

4.1: tetrahydrofuran / 48 h / 20 °C

5.1: oxygen; potassium fluoride / acetonitrile / 1 h / 20 °C

5.2: 48 h

With potassium fluoride; thionyl chloride; lithium telluride; oxygen; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1039/c6ob01836j