(2S,4R)-1-(4-Methoxy-benzyl)-3-methylene-5-oxo-4-(2-oxo-ethyl)-pyrrolidine-2,2-dicarboxylic acid benzyl ester tert-butyl ester

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Chemical Name:(2S,4R)-1-(4-Methoxy-benzyl)-3-methylene-5-oxo-4-(2-oxo-ethyl)-pyrrolidine-2,2-dicarboxylic acid benzyl ester tert-butyl ester
CAS No.:856681-97-5
Molecular Formula:C₂₈H₃₁NO₇
Molecular Weight:493.557
Hs Code.:

Synonyms:(2S,4R)-1-(4-Methoxy-benzyl)-3-methylene-5-oxo-4-(2-oxo-ethyl)-pyrrolidine-2,2-dicarboxylic acid benzyl ester tert-butyl ester

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Chemical Property of (2S,4R)-1-(4-Methoxy-benzyl)-3-methylene-5-oxo-4-(2-oxo-ethyl)-pyrrolidine-2,2-dicarboxylic acid benzyl ester tert-butyl ester

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Technology Process of (2S,4R)-1-(4-Methoxy-benzyl)-3-methylene-5-oxo-4-(2-oxo-ethyl)-pyrrolidine-2,2-dicarboxylic acid benzyl ester tert-butyl ester

There total 18 articles about (2S,4R)-1-(4-Methoxy-benzyl)-3-methylene-5-oxo-4-(2-oxo-ethyl)-pyrrolidine-2,2-dicarboxylic acid benzyl ester 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: 92.0%

: 856682-06-9
(2S,4R)-4-(2-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-3-methylene-5-oxo-pyrrolidine-2,2-dicarboxylic acid benzyl ester tert-butyl ester

: 856681-97-5
(2S,4R)-1-(4-Methoxy-benzyl)-3-methylene-5-oxo-4-(2-oxo-ethyl)-pyrrolidine-2,2-dicarboxylic acid benzyl ester tert-butyl ester

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1.5h;
DOI:10.1021/ja0522783

Reference yield: 72.0%

: 856682-05-8
(2S,3R,4R)-4-(2-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-5-oxo-3-phenylselanylmethyl-pyrrolidine-2,2-dicarboxylic acid benzyl ester tert-butyl ester

: 856681-97-5
(2S,4R)-1-(4-Methoxy-benzyl)-3-methylene-5-oxo-4-(2-oxo-ethyl)-pyrrolidine-2,2-dicarboxylic acid benzyl ester tert-butyl ester

: 856682-06-9
(2S,4R)-4-(2-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-3-methylene-5-oxo-pyrrolidine-2,2-dicarboxylic acid benzyl ester tert-butyl ester

Guidance literature:: With dihydrogen peroxide; In tetrahydrofuran; at 20 ℃; for 4h; Product distribution / selectivity;

Reference yield:

: 856682-02-5
Carbonic acid (2R,3R,4R)-4-(2-benzyloxy-ethyl)-2-hydroxymethyl-5-oxo-pyrrolidin-3-ylmethyl ester ethyl ester

: 856681-97-5
(2S,4R)-1-(4-Methoxy-benzyl)-3-methylene-5-oxo-4-(2-oxo-ethyl)-pyrrolidine-2,2-dicarboxylic acid benzyl ester tert-butyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: Jones reagent / acetone / 0 - 20 °C

2: 10.08 g / toluene / 1 h / Heating

3: 88 percent / K₂CO₃ / CH₂Cl₂ / 0 - 20 °C

4: 82 percent / LHMDS / tetrahydrofuran / 0.17 h / -20 °C

5: 90 percent / aq. HCl / tetrahydrofuran / 1 h / 0 °C

6: 62 percent / NaH / dimethylformamide / 0 - 20 °C

7: 100 percent / H₂ / Pd(OH)2/C / ethanol / 16 h / 760 Torr

8: NaBH₄ / ethanol / 4 h / 20 - 60 °C

9: 1.03 g / K₂CO₃ / dimethylformamide / 15 h / 20 °C

10: aq. H₂O₂ / tetrahydrofuran / 4 h / 20 °C

11: 174 mg / toluene / 2 h / 100 °C

With hydrogenchloride; sodium tetrahydroborate; jones reagent; hydrogen; dihydrogen peroxide; sodium hydride; potassium carbonate; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1: Jones' oxidation;
DOI:10.1021/ja0522783