(2R,3S,4S)-3-((S)-2-Hydroxy-but-3-enyl)-4-isopropenyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Base Information

• Chemical Name: (2R,3S,4S)-3-((S)-2-Hydroxy-but-3-enyl)-4-isopropenyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester
• CAS No.: 391677-15-9
• Molecular Formula: C₂₁H₂₇NO₅
• Molecular Weight: 373.449

Synonyms:(2R,3S,4S)-3-((S)-2-Hydroxy-but-3-enyl)-4-isopropenyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Chemical Property of (2R,3S,4S)-3-((S)-2-Hydroxy-but-3-enyl)-4-isopropenyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Chemical Property:

Purity/Quality:

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MSDS Files:

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Technology Process of (2R,3S,4S)-3-((S)-2-Hydroxy-but-3-enyl)-4-isopropenyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

There total 15 articles about (2R,3S,4S)-3-((S)-2-Hydroxy-but-3-enyl)-4-isopropenyl-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: 75.0%

methanol (67-56-1) + (3S,3aS,5S,7aR)-3-Isopropenyl-7-oxo-5-vinyl-hexahydro-pyrano[3,4-b]pyrrole-1-carboxylic acid benzyl ester (391677-13-7) → (2R,3S,4S)-3-((S)-2-Hydroxy-but-3-enyl)-4-isopropenyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (391677-15-9)

Guidance literature:

With sodium methylate; at 20 ℃;

DOI:10.1016/S0040-4039(01)01558-1

Reference yield:

(1R,3R,5R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2,9-dioxa-bicyclo[3.3.1]non-7-en-6-one → (2R,3S,4S)-3-((S)-2-Hydroxy-but-3-enyl)-4-isopropenyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (391677-15-9)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 98 percent / NaBH₄; CeCl₃*7H₂O / methanol / -78 °C

2.1: Et₃N / CH₂Cl₂

3.1: sodium azide / dimethylformamide / 80 °C

3.2: imidazole

4.1: LiAlH₄ / diethyl ether / 0 °C

5.1: K₂CO₃ / 0 °C

6.1: 83 percent / NaH / dimethylformamide / 0 °C

7.1: 98 percent / sodium hydrogen carbonate / diphenyl ether / 0.5 h / Heating

8.1: 97 percent / TBAF / tetrahydrofuran

9.1: Et₃N / CH₂Cl₂

10.1: LiI / tetrahydrofuran / Heating

11.1: 90 percent / zinc / methanol; acetic acid / Heating

12.1: 83 percent / TPAP-NMO / CH₂Cl₂; acetonitrile

13.1: 75 percent / NaOMe / 20 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; cerium(III) chloride; tetrapropylammonium perruthennate; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; sodium hydrogencarbonate; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; lithium iodide; zinc; In tetrahydrofuran; methanol; diphenylether; diethyl ether; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(01)01558-1

Reference yield:

(1R,3R,5R,6R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2,9-dioxa-bicyclo[3.3.1]non-7-en-6-ol → (2R,3S,4S)-3-((S)-2-Hydroxy-but-3-enyl)-4-isopropenyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (391677-15-9)

Guidance literature:

Multi-step reaction with 12 steps

1.1: Et₃N / CH₂Cl₂

2.1: sodium azide / dimethylformamide / 80 °C

2.2: imidazole

3.1: LiAlH₄ / diethyl ether / 0 °C

4.1: K₂CO₃ / 0 °C

5.1: 83 percent / NaH / dimethylformamide / 0 °C

6.1: 98 percent / sodium hydrogen carbonate / diphenyl ether / 0.5 h / Heating

7.1: 97 percent / TBAF / tetrahydrofuran

8.1: Et₃N / CH₂Cl₂

9.1: LiI / tetrahydrofuran / Heating

10.1: 90 percent / zinc / methanol; acetic acid / Heating

11.1: 83 percent / TPAP-NMO / CH₂Cl₂; acetonitrile

12.1: 75 percent / NaOMe / 20 °C

With lithium aluminium tetrahydride; sodium azide; tetrapropylammonium perruthennate; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; sodium hydrogencarbonate; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; lithium iodide; zinc; In tetrahydrofuran; methanol; diphenylether; diethyl ether; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(01)01558-1

upstream raw materials:

methanol

(3S,3aS,5S,7aR)-3-Isopropenyl-7-oxo-5-vinyl-hexahydro-pyrano[3,4-b]pyrrole-1-carboxylic acid benzyl ester

benzyl chloroformate

Downstream raw materials:

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

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

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