(2S)-5-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic Acid

Base Information

• Chemical Name: (2S)-5-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic Acid
• CAS No.: 158599-00-9
• Molecular Formula: C20H22N2O4
• Molecular Weight: 354.406
• European Community (EC) Number: 839-478-8
• Mol file: 158599-00-9.mol

Synonyms:Fmoc-Orn-OH;158599-00-9;(2S)-5-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic Acid;L-Ornithine, N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-aminopentanoic acid;(2S)-5-amino-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)pentanoic acid;(2S)-5-AMINO-2-(([(9H-FLUOREN-9-YL)METHOXY]CARBONYL)AMINO)PENTANOIC ACID;SCHEMBL5053659;ASLOVDWQFVNFRC-SFHVURJKSA-N;(9-fluorenyl)methoxycarbonyl-l-ornithine;AS-68955;E77133;EN300-258213;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-aminopentanoicacid

Chemical Property of (2S)-5-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic Acid

Chemical Property:

• Melting Point: 165.95 °C
• Boiling Point: 601.4±55.0 °C(Predicted)
• PKA: 3.74±0.21(Predicted)
• PSA: 0.00000
• Density: 1.268±0.06 g/cm3(Predicted)
• LogP: 0.00000
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 354.15795719
• Heavy Atom Count: 26
• Complexity: 476

Purity/Quality:

99%, ^*data from raw suppliers

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-aminopentanoicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CCCN)C(=O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CCCN)C(=O)O

Technology Process of (2S)-5-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic Acid

There total 5 articles about (2S)-5-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic Acid 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: 84.0%

Fmoc-Orn(Boc)-OH (109425-55-0,118476-89-4) → (S)-5-Amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid (158599-00-9)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 0.5h;

DOI:10.1016/j.tetlet.2005.09.044

Reference yield: 39.0%

Nα-(9-fluorenylmethyloxycarbonyl)-azido-L-ornithine (1097192-04-5,1176270-25-9) → (S)-5-Amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid (158599-00-9)

Guidance literature:

With chlorotriisopropylsilane; ethane-1,2-dithiol; trifluoroacetic acid; In water; at 20 ℃; for 2h;

DOI:10.1002/psc.1202

Reference yield:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (S)-5-Amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid (158599-00-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Cu(CH₃COO)2; NaOH / H₂O; acetone / 44 h

1.2: 8-quinolinol; Na₂CO₃ / acetone; H₂O / 1.5 h

1.3: H₂O; acetone / 1.5 h

2.1: p-toluenesulfonic acid hydrate; acetic acid / 0.5 h / Heating

2.2: 25.64 g / triethylamine / acetone; H₂O / 2 h

With sodium hydroxide; copper diacetate; toluene-4-sulfonic acid; acetic acid; In water; acetone;

upstream raw materials:

Fmoc-Orn(Boc)-OH

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

L-ornithine hydrochloride

N^α-(9-fluorenylmethyloxycarbonyl)-azido-L-ornithine

Downstream raw materials:

Fmoc-L-Orn(pNZ)-OH