N-9-fluorenylmethoxycarbonyl-(2S,3S)-3-fluoroprolyl-(2S,4R)-4-fluoroprolylglycine benzyl ester

Base Information

• Chemical Name: N-9-fluorenylmethoxycarbonyl-(2S,3S)-3-fluoroprolyl-(2S,4R)-4-fluoroprolylglycine benzyl ester
• CAS No.: 870992-74-8
• Molecular Formula: C₃₄H₃₃F₂N₃O₆
• Molecular Weight: 617.649
• Mol file: 870992-74-8.mol

Synonyms:N-9-fluorenylmethoxycarbonyl-(2S,3S)-3-fluoroprolyl-(2S,4R)-4-fluoroprolylglycine benzyl ester

Chemical Property of N-9-fluorenylmethoxycarbonyl-(2S,3S)-3-fluoroprolyl-(2S,4R)-4-fluoroprolylglycine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-9-fluorenylmethoxycarbonyl-(2S,3S)-3-fluoroprolyl-(2S,4R)-4-fluoroprolylglycine benzyl ester

There total 16 articles about N-9-fluorenylmethoxycarbonyl-(2S,3S)-3-fluoroprolyl-(2S,4R)-4-fluoroprolylglycine 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: 77.0%

N-9-fluorenylmethoxycarbonyl-(2S,3S)-3-fluoroproline (910642-53-4) + (2S,4R)-4-fluoroprolylglycine benzyl ester hydrochloride → N-9-fluorenylmethoxycarbonyl-(2S,3S)-3-fluoroprolyl-(2S,4R)-4-fluoroprolylglycine benzyl ester (870992-74-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In dichloromethane; at 0 - 20 ℃; for 21h;

DOI:10.1021/ja054674r

Reference yield:

N-tert-butoxycarbonyl-L-cis-4-hydroxyproline (87691-27-8,946610-68-0) → N-9-fluorenylmethoxycarbonyl-(2S,3S)-3-fluoroprolyl-(2S,4R)-4-fluoroprolylglycine benzyl ester (870992-74-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: Cs₂CO₃ / dimethylformamide / 0 °C

1.2: 95 percent / dimethylformamide

2.1: 36 percent / morph-DAST / tetrahydrofuran / 48 h / -78 - 20 °C

3.1: 100 percent / H₂ / Pd/C / methanol / 18 h

4.1: 79 percent / iPr₂NEt; PyBOP / CH₂Cl₂

5.1: 100 percent / HCl / dioxane / 1 h

6.1: 77 percent / PyBroP; DIEA / CH₂Cl₂ / 21 h / 0 - 20 °C

With hydrogenchloride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; caesium carbonate; N-ethyl-N,N-diisopropylamine; morpholinosulfur trifluoride; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja054674r

Reference yield:

(2S,4S)-2-benzyl 1-tert-butyl 4-hydroxypyrrolidine-1,2-dicarboxylate (132622-90-3) → N-9-fluorenylmethoxycarbonyl-(2S,3S)-3-fluoroprolyl-(2S,4R)-4-fluoroprolylglycine benzyl ester (870992-74-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 36 percent / morph-DAST / tetrahydrofuran / 48 h / -78 - 20 °C

2: 100 percent / H₂ / Pd/C / methanol / 18 h

3: 79 percent / iPr₂NEt; PyBOP / CH₂Cl₂

4: 100 percent / HCl / dioxane / 1 h

5: 77 percent / PyBroP; DIEA / CH₂Cl₂ / 21 h / 0 - 20 °C

With hydrogenchloride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; N-ethyl-N,N-diisopropylamine; morpholinosulfur trifluoride; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;

DOI:10.1021/ja054674r

upstream raw materials:

N-9-fluorenylmethoxycarbonyl-(2S,3S)-3-fluoroproline

(2R,3S)-3-Fluoro-pyrrolidine-2-carboxylic acid

N-tert-butoxycarbonyl-(2S,4R)-4-fluoroprolylglycine benzyl ester

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide