(2S,4R)-4-Acetylsulfanyl-pyrrolidine-1,2-dicarboxylic acid 2-(4-methoxy-benzyl) ester 1-(4-nitro-benzyl) ester

Base Information

• Chemical Name: (2S,4R)-4-Acetylsulfanyl-pyrrolidine-1,2-dicarboxylic acid 2-(4-methoxy-benzyl) ester 1-(4-nitro-benzyl) ester
• CAS No.: 248604-44-6
• Molecular Formula: C₂₃H₂₄N₂O₈S
• Molecular Weight: 488.518

Synonyms:(2S,4R)-4-Acetylsulfanyl-pyrrolidine-1,2-dicarboxylic acid 2-(4-methoxy-benzyl) ester 1-(4-nitro-benzyl) ester

Chemical Property of (2S,4R)-4-Acetylsulfanyl-pyrrolidine-1,2-dicarboxylic acid 2-(4-methoxy-benzyl) ester 1-(4-nitro-benzyl) ester

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Technology Process of (2S,4R)-4-Acetylsulfanyl-pyrrolidine-1,2-dicarboxylic acid 2-(4-methoxy-benzyl) ester 1-(4-nitro-benzyl) ester

There total 3 articles about (2S,4R)-4-Acetylsulfanyl-pyrrolidine-1,2-dicarboxylic acid 2-(4-methoxy-benzyl) ester 1-(4-nitro-benzyl) 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: 83.0%

tiolacetic acid (507-09-5) + (2S,4S)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 2-(4-methoxy-benzyl) ester 1-(4-nitro-benzyl) ester (96035-12-0) → (2S,4R)-4-Acetylsulfanyl-pyrrolidine-1,2-dicarboxylic acid 2-(4-methoxy-benzyl) ester 1-(4-nitro-benzyl) ester (248604-44-6)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1016/S0960-894X(99)00407-2

Reference yield:

(2S,4S)-4-Formyloxy-pyrrolidine-1,2-dicarboxylic acid 2-(4-methoxy-benzyl) ester 1-(4-nitro-benzyl) ester (130625-68-2) → (2S,4R)-4-Acetylsulfanyl-pyrrolidine-1,2-dicarboxylic acid 2-(4-methoxy-benzyl) ester 1-(4-nitro-benzyl) ester (248604-44-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / 1 N NaOH / ethanol / 0.5 h / 0 °C

2: 83 percent / PPh₃, DEAD / tetrahydrofuran

With sodium hydroxide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; ethanol;

DOI:10.1016/S0960-894X(99)00407-2

Reference yield:

(2S,4R)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 2-(4-methoxy-benzyl) ester 1-(4-nitro-benzyl) ester → (2S,4R)-4-Acetylsulfanyl-pyrrolidine-1,2-dicarboxylic acid 2-(4-methoxy-benzyl) ester 1-(4-nitro-benzyl) ester (248604-44-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / PPh₃, DEAD / tetrahydrofuran

2: 90 percent / 1 N NaOH / ethanol / 0.5 h / 0 °C

3: 83 percent / PPh₃, DEAD / tetrahydrofuran

With sodium hydroxide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; ethanol;

DOI:10.1016/S0960-894X(99)00407-2

upstream raw materials:

tiolacetic acid

(2S,4S)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 2-(4-methoxy-benzyl) ester 1-(4-nitro-benzyl) ester

(2S,4S)-4-Formyloxy-pyrrolidine-1,2-dicarboxylic acid 2-(4-methoxy-benzyl) ester 1-(4-nitro-benzyl) ester

Downstream raw materials:

(4R,5S,6S)-3-[(3R,5S)-5-((3R,4R)-3,4-Dihydroxy-pyrrolidine-1-carbonyl)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(4R,5S,6S)-3-[(3R,5S)-5-((3S,4S)-3,4-Dihydroxy-pyrrolidine-1-carbonyl)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(2S,4R)-4-Acetylsulfanyl-2-((3R,4R)-3,4-dihydroxy-pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

(2S,4R)-4-Acetylsulfanyl-2-((3S,4S)-3,4-dihydroxy-pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

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