(2R,3S,4S)-4-Isopropenyl-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Base Information

• Chemical Name: (2R,3S,4S)-4-Isopropenyl-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester
• CAS No.: 120229-02-9
• Molecular Formula: C₂₀H₂₅NO₆
• Molecular Weight: 375.422

Synonyms:(2R,3S,4S)-4-Isopropenyl-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Chemical Property of (2R,3S,4S)-4-Isopropenyl-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S)-4-Isopropenyl-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

There total 38 articles about (2R,3S,4S)-4-Isopropenyl-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-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: 80.0%

(2R,3S,4S)-4-(1-Chloromethyl-vinyl)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (120229-01-8) → (2R,3S,4S)-4-Isopropenyl-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (120229-02-9)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 3h; Heating;

DOI:10.1039/c39880001204

Reference yield:

Benzyl N-hydroxycarbamate (3426-71-9) → (2R,3S,4S)-4-Isopropenyl-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (120229-02-9)

Guidance literature:

Multi-step reaction with 15 steps

1: NaIO₄ / methanol; H₂O

2: Mo(CO)6 / acetonitrile; H₂O

3: 49 percent / lipase AK (pseudomonas fluorescens, Amano) / CH₂Cl₂ / 48 h / 20 °C

4: 98 percent / K₂CO₃ / methanol

5: 91 percent / imidazole / dimethylformamide

6: OsO₄; NMO / tetrahydrofuran; H₂O

7: PPTS / dimethylformamide

8: NaI; NaH / tetrahydrofuran

9: TBAF / tetrahydrofuran

10: 92 percent / NaH / tetrahydrofuran / -30 °C

11: 72 percent / NaHCO₃ / diphenyl ether / 0.75 h / Heating

12: HCl / tetrahydrofuran; H₂O / Heating

13: NaIO₄ / tetrahydrofuran; H₂O

14: Jones reagent

With 1H-imidazole; hydrogenchloride; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; jones reagent; hexacarbonyl molybdenum; lipase AK (pseudomonas fluorescens, Amano); tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; sodium hydrogencarbonate; potassium carbonate; sodium iodide; In tetrahydrofuran; methanol; diphenylether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1: Oxidation / 2: Ring cleavage / 3: Acetylation / 4: Substitution / 5: silylation / 6: hydroxylation / 7: Cyclization / 8: Substitution / 9: desilylation / 10: Addition / 11: Rearrangement / 12: Ring cleavage / 13: Oxidation / 14: Jones' oxidation / 15: Methylation;

DOI:10.1021/ol006377r

Reference yield:

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (2R,3S,4S)-4-Isopropenyl-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (120229-02-9)

Guidance literature:

Multi-step reaction with 15 steps

1: NaIO₄ / methanol; H₂O

2: Mo(CO)6 / acetonitrile; H₂O

3: 49 percent / lipase AK (pseudomonas fluorescens, Amano) / CH₂Cl₂ / 48 h / 20 °C

4: 98 percent / K₂CO₃ / methanol

5: 91 percent / imidazole / dimethylformamide

6: OsO₄; NMO / tetrahydrofuran; H₂O

7: PPTS / dimethylformamide

8: NaI; NaH / tetrahydrofuran

9: TBAF / tetrahydrofuran

10: 92 percent / NaH / tetrahydrofuran / -30 °C

11: 72 percent / NaHCO₃ / diphenyl ether / 0.75 h / Heating

12: HCl / tetrahydrofuran; H₂O / Heating

13: NaIO₄ / tetrahydrofuran; H₂O

14: Jones reagent

With 1H-imidazole; hydrogenchloride; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; jones reagent; hexacarbonyl molybdenum; lipase AK (pseudomonas fluorescens, Amano); tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; sodium hydrogencarbonate; potassium carbonate; sodium iodide; In tetrahydrofuran; methanol; diphenylether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1: Oxidation / 2: Ring cleavage / 3: Acetylation / 4: Substitution / 5: silylation / 6: hydroxylation / 7: Cyclization / 8: Substitution / 9: desilylation / 10: Addition / 11: Rearrangement / 12: Ring cleavage / 13: Oxidation / 14: Jones' oxidation / 15: Methylation;

DOI:10.1021/ol006377r

upstream raw materials:

(2R,3S,4S)-4-(1-Chloromethyl-vinyl)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

diazomethane

benzyl chloroformate

(2R,3S,4S)-4-Isopropenyl-3-(2-oxo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Downstream raw materials:

(2S,3S,4S)-N-(benzyloxycarbonyl)-2-carboxy-4-(1-methylethenyl)pyrrolidine-3-acetic acid

1-(benzyloxycarbonyl)kainic acid dimethyl ester

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