(R_S,S)-(-)-methyl-3-oxo-N-(p-toluenesulfinyl)-5-amino-5-(3,4-dimethoxyphenyl)pentanoate

Base Information

• Chemical Name: (R_S,S)-(-)-methyl-3-oxo-N-(p-toluenesulfinyl)-5-amino-5-(3,4-dimethoxyphenyl)pentanoate
• CAS No.: 299209-93-1
• Molecular Formula: C₂₁H₂₅NO₆S
• Molecular Weight: 419.499

Synonyms:(R_S,S)-(-)-methyl-3-oxo-N-(p-toluenesulfinyl)-5-amino-5-(3,4-dimethoxyphenyl)pentanoate

Chemical Property of (R_S,S)-(-)-methyl-3-oxo-N-(p-toluenesulfinyl)-5-amino-5-(3,4-dimethoxyphenyl)pentanoate

Chemical Property:

Purity/Quality:

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Technology Process of (R_S,S)-(-)-methyl-3-oxo-N-(p-toluenesulfinyl)-5-amino-5-(3,4-dimethoxyphenyl)pentanoate

There total 10 articles about (R_S,S)-(-)-methyl-3-oxo-N-(p-toluenesulfinyl)-5-amino-5-(3,4-dimethoxyphenyl)pentanoate 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: 93.0%

(RS,S)-(-)-methyl-N-(p-toluenesulfinyl)-3-amino-3-(3,4-dimethoxyphenyl)propanoate (299210-11-0) + acetic acid methyl ester (79-20-9) → (RS,S)-(-)-methyl-3-oxo-N-(p-toluenesulfinyl)-5-amino-5-(3,4-dimethoxyphenyl)pentanoate (299209-93-1)

Guidance literature:

acetic acid methyl ester; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h;

(R_S,S)-(-)-methyl-N-(p-toluenesulfinyl)-3-amino-3-(3,4-dimethoxyphenyl)propanoate; In tetrahydrofuran; at -78 ℃; for 4h; Further stages.;

DOI:10.1021/ol0061438

Reference yield: 85.0%

acetic acid methyl ester (79-20-9) + (R)-(+)-(3,4-dimethoxybenzylidene)-p-toluenesulfinamide (299209-91-9) → (RS,S)-(-)-methyl-3-oxo-N-(p-toluenesulfinyl)-5-amino-5-(3,4-dimethoxyphenyl)pentanoate (299209-93-1)

Guidance literature:

acetic acid methyl ester; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h;

(R)-(+)-(3,4-dimethoxybenzylidene)-p-toluenesulfinamide; In tetrahydrofuran; at -78 ℃; for 3.5h; Further stages.;

DOI:10.1021/ol0061438

Reference yield:

3,4-dimethoxy-benzaldehyde (120-14-9) → (RS,S)-(-)-methyl-3-oxo-N-(p-toluenesulfinyl)-5-amino-5-(3,4-dimethoxyphenyl)pentanoate (299209-93-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 95 percent / titanium (IV) ethoxide / CH₂Cl₂ / 1.5 h / 20 °C

2.1: NaHMDS / diethyl ether; tetrahydrofuran / 0.83 h / -78 °C

2.2: 80 percent / diethyl ether; tetrahydrofuran / 4 h / -78 °C

3.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

3.2: 93 percent / tetrahydrofuran / 4 h / -78 °C

With titanium(IV) tetraethanolate; sodium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Condensation / 2.1: Metallation / 2.2: Addition / 3.1: Metallation / 3.2: Addition;

DOI:10.1021/ol0061438

upstream raw materials:

acetic acid methyl ester

(R)-(+)-(3,4-dimethoxybenzylidene)-p-toluenesulfinamide

(R_S,S)-(-)-methyl-N-(p-toluenesulfinyl)-3-amino-3-(3,4-dimethoxyphenyl)propanoate

3,4-dimethoxy-benzaldehyde

Downstream raw materials:

(R_S,1S,3R)-(-)-1-N-(p-toluenesulfinyl)amino 1-(3,4-dimethoxyphenyl)-3-hydroxy-5-oxo-9-benzyloxynonane

(R_S,3R,5S)-(-)-methoxy-N-methyl-3-hydroxy-5-(3,4-dimethoxyphenyl)-5-N-(p-toluenesulfinyl)pentanamide

(2S,4S,6S)-(-)-2-(4-benzyloxy-butyl)-6-(3,4-dimethoxy-phenyl)-piperidin-4-ol

(4R,6S)-(-)-4-hydroxy-6-(3,4-dimethoxyphenyl)-piperidine-2-one

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