(4S)-1-(tert-butoxycarbonyl)-4-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-D-proline

Base Information

• Chemical Name: (4S)-1-(tert-butoxycarbonyl)-4-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-D-proline
• CAS No.: 1018332-23-4
• Molecular Formula: C₂₅H₂₈N₂O₆
• Molecular Weight: 452.507

Synonyms:

Chemical Property of (4S)-1-(tert-butoxycarbonyl)-4-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-D-proline

Chemical Property:

• Boiling Point: 650.2±55.0 °C(Predicted)
• Density: 1.33±0.1 g/cm3(Predicted)

Purity/Quality:

97% ^*data from raw suppliers

Boc-D-Pro(4-NHFmoc)-OH(2R,4S) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (4S)-1-(tert-butoxycarbonyl)-4-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-D-proline

There total 3 articles about (4S)-1-(tert-butoxycarbonyl)-4-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-D-proline 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: 75.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (4S)-1-(tert-butoxycarbonyl)-4-amino-D-proline (132622-78-7) → (4S)-1-(tert-butoxycarbonyl)-4-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-D-proline (1018332-23-4)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; water; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acsmedchemlett.0c00029

Reference yield:

(4R)-1-(tert-butoxycarbonyl)-4-hydroxy-D-proline (135042-12-5,946610-68-0) → (4S)-1-(tert-butoxycarbonyl)-4-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-D-proline (1018332-23-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: caesium carbonate / methanol; water / Inert atmosphere; Cooling with ice

1.2: 20 h / 0 - 20 °C / Inert atmosphere

2.1: diphenyl phosphoryl azide; triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 40.5 h / 5 - 20 °C / Inert atmosphere

3.1: palladium 10% on activated carbon; hydrogen / methanol / 15 h / 20 °C

4.1: sodium carbonate / water; tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

With di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; palladium 10% on activated carbon; hydrogen; sodium carbonate; caesium carbonate; triphenylphosphine; In tetrahydrofuran; methanol; water;

DOI:10.1021/acsmedchemlett.0c00029

Reference yield:

2-benzyl 1-(tert-butyl) (2R,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate (132622-92-5) → (4S)-1-(tert-butoxycarbonyl)-4-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-D-proline (1018332-23-4)

Guidance literature:

Multi-step reaction with 3 steps

1: diphenyl phosphoryl azide; triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 40.5 h / 5 - 20 °C / Inert atmosphere

2: palladium 10% on activated carbon; hydrogen / methanol / 15 h / 20 °C

3: sodium carbonate / water; tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

With di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; palladium 10% on activated carbon; hydrogen; sodium carbonate; triphenylphosphine; In tetrahydrofuran; methanol; water;

DOI:10.1021/acsmedchemlett.0c00029

upstream raw materials:

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

(4S)-1-(tert-butoxycarbonyl)-4-amino-D-proline

(4R)-1-(tert-butoxycarbonyl)-4-hydroxy-D-proline

2-benzyl 1-(tert-butyl) (2R,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate

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