(2S,5S)-5-[(2S,4R)-1-Acetyl-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carbonylsulfanylmethyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Base Information

• Chemical Name: (2S,5S)-5-[(2S,4R)-1-Acetyl-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carbonylsulfanylmethyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
• CAS No.: 161424-47-1
• Molecular Formula: C₂₆H₃₆N₂O₉S₂
• Molecular Weight: 584.712
• Mol file: 161424-47-1.mol

Synonyms:(2S,5S)-5-[(2S,4R)-1-Acetyl-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carbonylsulfanylmethyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Chemical Property of (2S,5S)-5-[(2S,4R)-1-Acetyl-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carbonylsulfanylmethyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5S)-5-[(2S,4R)-1-Acetyl-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carbonylsulfanylmethyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

There total 7 articles about (2S,5S)-5-[(2S,4R)-1-Acetyl-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carbonylsulfanylmethyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl 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: 91.0%

(2S-trans)-5-(Mercaptomethyl)-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-methyl diester (161424-46-0) + N-acetyl-trans-4-(tosyloxy)-L-proline (100895-61-2) → (2S,5S)-5-[(2S,4R)-1-Acetyl-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carbonylsulfanylmethyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (161424-47-1)

Guidance literature:

With 1,1'-carbonyldiimidazole; In acetonitrile; 1.) 0 deg C, 1 h, 2.) 0 deg C, 2 h; 23 deg C, 22 h;

DOI:10.1021/jo00107a028

Reference yield:

(S)-N-(tert-butoxycarbonyl)proline methyl ester (59936-29-7) → (2S,5S)-5-[(2S,4R)-1-Acetyl-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carbonylsulfanylmethyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (161424-47-1)

Guidance literature:

Multi-step reaction with 7 steps

1: Bu₄NBF₄ / 18 h / 23 °C / electrolysis: 260 mA, graphite plates

2: 1.) CuBr*DMS, 2.) BF₃*Et₂O / 1.) Et₂O, -50 deg C to -40 deg C, 30 min, 2.) Et₂O, -78 deg C, 10 min; -78 deg C to r.t., 5 h

3: 1.) O₃, 2.) dimethyl sulfide / 1.) MeOH, -78 deg C, 2.) CH₂Cl₂, -78 deg C to r.t., 12 h

4: NaBH₄ / methanol / 1 h / 0 °C

5: 94 percent / PPh₃, diisopropyl azodicarboxylate / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) 0 deg C, 2 h; 23 deg C, 1 h

6: 85 percent / NH₃ / methanol / 2 h / 23 °C

7: 91 percent / 1,1'-carbonyldiimidazole / acetonitrile / 1.) 0 deg C, 1 h, 2.) 0 deg C, 2 h; 23 deg C, 22 h

With sodium tetrahydroborate; copper(I) bromide dimethylsulfide complex; dimethylsulfide; di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; tetrabutylammonium tetrafluoroborate; ammonia; ozone; triphenylphosphine; 1,1'-carbonyldiimidazole; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1021/jo00107a028

Reference yield:

(2S-trans)-5-(Hydroxymethyl)-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-methyl diester (136175-14-9) → (2S,5S)-5-[(2S,4R)-1-Acetyl-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carbonylsulfanylmethyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (161424-47-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / PPh₃, diisopropyl azodicarboxylate / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) 0 deg C, 2 h; 23 deg C, 1 h

2: 85 percent / NH₃ / methanol / 2 h / 23 °C

3: 91 percent / 1,1'-carbonyldiimidazole / acetonitrile / 1.) 0 deg C, 1 h, 2.) 0 deg C, 2 h; 23 deg C, 22 h

With di-isopropyl azodicarboxylate; ammonia; triphenylphosphine; 1,1'-carbonyldiimidazole; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1021/jo00107a028

upstream raw materials:

(2S-trans)-5-(Mercaptomethyl)-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-methyl diester

N-acetyl-trans-4-(tosyloxy)-L-proline

(S)-N-(tert-butoxycarbonyl)proline methyl ester

(2S-trans)-5-(Hydroxymethyl)-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-methyl diester