(2R,3R,4S)-2-acetoxymethyl-3-benzyloxymethyl-3-hydroxy-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2R,3R,4S)-2-acetoxymethyl-3-benzyloxymethyl-3-hydroxy-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester
CAS No.:1373929-31-7
Molecular Formula:C₁₈H₂₃NO₇
Molecular Weight:365.383
Hs Code.:

Synonyms:(2R,3R,4S)-2-acetoxymethyl-3-benzyloxymethyl-3-hydroxy-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

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Chemical Property of (2R,3R,4S)-2-acetoxymethyl-3-benzyloxymethyl-3-hydroxy-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

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Technology Process of (2R,3R,4S)-2-acetoxymethyl-3-benzyloxymethyl-3-hydroxy-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

There total 9 articles about (2R,3R,4S)-2-acetoxymethyl-3-benzyloxymethyl-3-hydroxy-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl 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: 90.0%

: 1373929-25-9
(2R,3R,4S)-3-benzyloxymethyl-3-hydroxy-2-hydroxymethyl-4-methyl-5-oxopyrrolidine-2-carboxylic acid methyl ester

: 75-36-5
acetyl chloride

: 1373929-31-7
(2R,3R,4S)-2-acetoxymethyl-3-benzyloxymethyl-3-hydroxy-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

Guidance literature:: (2R,3R,4S)-3-benzyloxymethyl-3-hydroxy-2-hydroxymethyl-4-methyl-5-oxopyrrolidine-2-carboxylic acid methyl ester; acetyl chloride; With dmap; triethylamine; In tetrahydrofuran; at 20 ℃; for 0.25h;

With hydrogenchloride; In tetrahydrofuran; water;
DOI:10.1039/c2ob00042c

Reference yield:

: 61795-51-5
benzyl 4-(benzyloxy)-3-oxobutanoate

: 1373929-31-7
(2R,3R,4S)-2-acetoxymethyl-3-benzyloxymethyl-3-hydroxy-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium tert-butylate / tetrahydrofuran / 0.67 h / 0 - 20 °C

1.2: 5 h

2.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 5.25 h / 0 - 20 °C

3.1: sodium methylate / methanol / 24 h / 20 °C

4.1: 1.3-propanedithiol; hydrogenchloride / 2,2,2-trifluoroethanol; water / 24 h / 20 °C

5.1: dmap; triethylamine / tetrahydrofuran / 0.25 h / 20 °C

With 1.3-propanedithiol; hydrogenchloride; dmap; potassium tert-butylate; sodium methylate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 2,2,2-trifluoroethanol; water;
DOI:10.1039/c2ob00042c

Reference yield:

: 67354-37-4
4-(benzyloxy)-3-oxobutanoic acid

: 1373929-31-7
(2R,3R,4S)-2-acetoxymethyl-3-benzyloxymethyl-3-hydroxy-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 5.25 h / 0 - 20 °C

2.1: sodium methylate / methanol / 20 °C / Inert atmosphere

3.1: lithium diisopropyl amide / tetrahydrofuran; methanol / 0.5 h / -10 °C / Inert atmosphere

3.2: 1.5 h / Inert atmosphere

4.1: 1.3-propanedithiol; hydrogenchloride / 2,2,2-trifluoroethanol; water / 24 h / 20 °C

5.1: dmap; triethylamine / tetrahydrofuran / 0.25 h / 20 °C

With 1.3-propanedithiol; hydrogenchloride; dmap; sodium methylate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; 2,2,2-trifluoroethanol; water;
DOI:10.1039/c2ob00042c