(S)-2-{(S)-3-[(S)-3-((S)-3-Acetoxy-3-benzyloxycarbonyl-propionyloxy)-3-benzyloxycarbonyl-propionyloxy]-3-benzyloxycarbonyl-propionyloxy}-succinic acid 1-benzyl ester

Base Information

• Chemical Name: (S)-2-{(S)-3-[(S)-3-((S)-3-Acetoxy-3-benzyloxycarbonyl-propionyloxy)-3-benzyloxycarbonyl-propionyloxy]-3-benzyloxycarbonyl-propionyloxy}-succinic acid 1-benzyl ester
• CAS No.: 276871-13-7
• Molecular Formula: C₄₆H₄₄O₁₈
• Molecular Weight: 884.845
• Mol file: 276871-13-7.mol

Synonyms:(S)-2-{(S)-3-[(S)-3-((S)-3-Acetoxy-3-benzyloxycarbonyl-propionyloxy)-3-benzyloxycarbonyl-propionyloxy]-3-benzyloxycarbonyl-propionyloxy}-succinic acid 1-benzyl ester

Chemical Property of (S)-2-{(S)-3-[(S)-3-((S)-3-Acetoxy-3-benzyloxycarbonyl-propionyloxy)-3-benzyloxycarbonyl-propionyloxy]-3-benzyloxycarbonyl-propionyloxy}-succinic acid 1-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-{(S)-3-[(S)-3-((S)-3-Acetoxy-3-benzyloxycarbonyl-propionyloxy)-3-benzyloxycarbonyl-propionyloxy]-3-benzyloxycarbonyl-propionyloxy}-succinic acid 1-benzyl ester

There total 7 articles about (S)-2-{(S)-3-[(S)-3-((S)-3-Acetoxy-3-benzyloxycarbonyl-propionyloxy)-3-benzyloxycarbonyl-propionyloxy]-3-benzyloxycarbonyl-propionyloxy}-succinic acid 1-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: 78.0%

(S)-2-[(S)-3-((S)-3-Acetoxy-3-benzyloxycarbonyl-propionyloxy)-3-benzyloxycarbonyl-propionyloxy]-succinic acid 4-((S)-2-allyloxycarbonyl-1-benzyloxycarbonyl-ethyl) ester 1-benzyl ester (276871-12-6) → (S)-2-{(S)-3-[(S)-3-((S)-3-Acetoxy-3-benzyloxycarbonyl-propionyloxy)-3-benzyloxycarbonyl-propionyloxy]-3-benzyloxycarbonyl-propionyloxy}-succinic acid 1-benzyl ester (276871-13-7)

Guidance literature:

With 1H-imidazole; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1002/1099-0690(200004)2000:7<1207::AID-EJOC1207>3.0.CO;2-2

Reference yield:

(S)-3-(Benzyloxycarbonyl)-3-hydroxypropanoic acid (66178-04-9) → (S)-2-{(S)-3-[(S)-3-((S)-3-Acetoxy-3-benzyloxycarbonyl-propionyloxy)-3-benzyloxycarbonyl-propionyloxy]-3-benzyloxycarbonyl-propionyloxy}-succinic acid 1-benzyl ester (276871-13-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 92 percent / K₂CO₃; tetrabutyl ammonium bromide / dimethylformamide / 4 h / 20 °C

2: 5.96 g / pyridine / CH₂Cl₂ / -78 - 20 °C

3: 95 percent / 70percent HF / CH₂Cl₂; pyridine / 14 h / 0 - 20 °C

4: 2.71 g / pyridine / CH₂Cl₂ / -78 - 20 °C

5: 87 percent / 70percent HF / pyridine; CH₂Cl₂ / 22 h / 20 °C

6: 97 percent / pyridine; CH₂Cl₂ / 0.92 h / -10 °C

7: 78 percent / imidazole / Pd(PPh₃)4 / tetrahydrofuran / 2 h / 20 °C

With pyridine; 1H-imidazole; tetrabutylammomium bromide; potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide; 1: Esterification / 2: Substitution / 3: Hydrolysis / 4: Condensation / 5: Hydrolysis / 6: Acetylation / 7: Ester cleavage;

DOI:10.1002/1099-0690(200004)2000:7<1207::AID-EJOC1207>3.0.CO;2-2

Reference yield:

4-allyl 1-benzyl (2S)-2-hydroxybutanedioate (276870-98-5) → (S)-2-{(S)-3-[(S)-3-((S)-3-Acetoxy-3-benzyloxycarbonyl-propionyloxy)-3-benzyloxycarbonyl-propionyloxy]-3-benzyloxycarbonyl-propionyloxy}-succinic acid 1-benzyl ester (276871-13-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 5.96 g / pyridine / CH₂Cl₂ / -78 - 20 °C

2: 95 percent / 70percent HF / CH₂Cl₂; pyridine / 14 h / 0 - 20 °C

3: 2.71 g / pyridine / CH₂Cl₂ / -78 - 20 °C

4: 87 percent / 70percent HF / pyridine; CH₂Cl₂ / 22 h / 20 °C

5: 97 percent / pyridine; CH₂Cl₂ / 0.92 h / -10 °C

6: 78 percent / imidazole / Pd(PPh₃)4 / tetrahydrofuran / 2 h / 20 °C

With pyridine; 1H-imidazole; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; pyridine; dichloromethane; 1: Substitution / 2: Hydrolysis / 3: Condensation / 4: Hydrolysis / 5: Acetylation / 6: Ester cleavage;

DOI:10.1002/1099-0690(200004)2000:7<1207::AID-EJOC1207>3.0.CO;2-2

upstream raw materials:

(S)-2-[(S)-3-((S)-3-Acetoxy-3-benzyloxycarbonyl-propionyloxy)-3-benzyloxycarbonyl-propionyloxy]-succinic acid 4-((S)-2-allyloxycarbonyl-1-benzyloxycarbonyl-ethyl) ester 1-benzyl ester

(S)-3-(Benzyloxycarbonyl)-3-hydroxypropanoic acid

4-allyl 1-benzyl (2S)-2-hydroxybutanedioate

4-allyl 1-benzyl (2S)-2-[(3S)-3-benzyloxycarbonyl-3-hydroxypropanoyloxy]butanedioate