(3R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-oxo-3-((E)-3-phenyl-allyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(3R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-oxo-3-((E)-3-phenyl-allyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:129413-76-9
Molecular Formula:C₂₅H₃₉NO₄Si
Molecular Weight:445.674
Hs Code.:

Synonyms:(3R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-oxo-3-((E)-3-phenyl-allyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (3R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-oxo-3-((E)-3-phenyl-allyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of (3R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-oxo-3-((E)-3-phenyl-allyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 1 articles about (3R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-oxo-3-((E)-3-phenyl-allyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 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:

: 81658-26-6
tert-butyl (S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxopyrrolidin-1-carboxylate

: 4392-24-9
Cinnamyl bromide

: 129413-76-9
(3R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-oxo-3-((E)-3-phenyl-allyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With lithium diisopropyl amide; Yield given. Multistep reaction; 1.) THF, -78 deg C, 30 min, 2.) -78 deg C;
DOI:10.3987/COM-89-5216

Reference yield: 98.0%

: 129413-76-9
(3R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-oxo-3-((E)-3-phenyl-allyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

: 129413-79-2
(3R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-oxo-3-(3-phenyl-propyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With hydrogen; palladium on activated charcoal;
DOI:10.3987/COM-89-5216

Reference yield:

: 129413-76-9
(3R,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-oxo-3-((E)-3-phenyl-allyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

: 129413-93-0
(2S,4R)-2-amino-4-(3-phenylpropyl)pentanedioic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 98 percent / H₂ / 10percent Pd/C

2: 76 percent / LiOH, H₂O / tetrahydrofuran / 0 - 20 °C

3: 76 percent / PTSA / Ambient temperature

4: 73 percent / 1N aq. NaOH / tetrahydrofuran / 0 °C

5: 70 percent / 0 °C / Jones oxidation

6: 82 percent / TFA / CH₂Cl₂ / 0 °C

With lithium hydroxide; sodium hydroxide; water; hydrogen; toluene-4-sulfonic acid; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane;
DOI:10.3987/COM-89-5216