L-Ornithine, N5-(aMinocarbonyl)-N2-[N-[(9H-fluoren-9-ylMethoxy)carbonyl]-L-valyl]-

Base Information

• Chemical Name: L-Ornithine, N5-(aMinocarbonyl)-N2-[N-[(9H-fluoren-9-ylMethoxy)carbonyl]-L-valyl]-
• CAS No.: 159858-21-6
• Molecular Formula: C₂₆H₃₂N₄O₆
• Molecular Weight: 496.563
• Mol file: 159858-21-6.mol

Synonyms:(S)-2-((S)-2-((((9H-fluoren-9-yl)-methoxy)carbonyl)amino)-3-methylbutanamido)-5-ureidopentanoic acid

Chemical Property of L-Ornithine, N5-(aMinocarbonyl)-N2-[N-[(9H-fluoren-9-ylMethoxy)carbonyl]-L-valyl]-

Chemical Property:

• Boiling Point: 787.1±60.0 °C(Predicted)
• PKA: 3.41±0.10(Predicted)
• Density: 1.269±0.06 g/cm3(Predicted)

Purity/Quality:

98.0% ^*data from raw suppliers

Fmoc-Val-Cit-OH 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-Ornithine, N5-(aMinocarbonyl)-N2-[N-[(9H-fluoren-9-ylMethoxy)carbonyl]-L-valyl]-

There total 8 articles about L-Ornithine, N5-(aMinocarbonyl)-N2-[N-[(9H-fluoren-9-ylMethoxy)carbonyl]-L-valyl]- 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: 98.0%

Citrulline (372-75-8) + 2,5-dioxopyrrolidin-1-yl-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valinate (130878-68-1) → (S)-2-((S)-2-((((9H-fluoren-9-yl)-methoxy)carbonyl)amino)-3-methylbutanamido)-5-ureidopentanoic acid (159858-21-6)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; 1,2-dimethoxyethane; water; at 0 - 20 ℃; for 28h;

Reference yield: 80.0%

→ (S)-2-((S)-2-((((9H-fluoren-9-yl)-methoxy)carbonyl)amino)-3-methylbutanamido)-5-ureidopentanoic acid (159858-21-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 5h;

With piperidine; In N,N-dimethyl-formamide; at 20 ℃; for 1h; Further stages;

Reference yield: 70.0%

Citrulline (372-75-8) + Fmoc-Val-OH (68858-20-8) → (S)-2-((S)-2-((((9H-fluoren-9-yl)-methoxy)carbonyl)amino)-3-methylbutanamido)-5-ureidopentanoic acid (159858-21-6)

Guidance literature:

Fmoc-Val-OH; With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 20 ℃; for 16h;

Citrulline; With sodium hydrogencarbonate; In tetrahydrofuran; 1,2-dimethoxyethane; water; at 20 ℃; for 16h;

DOI:10.3390/ijms18091860

upstream raw materials:

Citrulline

2,5-dioxopyrrolidin-1-yl-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valinate

Fmoc-Val-OH

D-citrulline

Downstream raw materials:

(9H-fluorenyl)methyl ((S)-1-(((S)-1-(((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidovalerylamido-2-yl)amino))-3-methylbutyramido-2-yl)-carbamate

(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide

C₂₉H₄₂N₆O₁₁S₂

C₃₆H₄₅N₇O₁₅S₂

Refernces

• 1、 -. "ANTIBODY-DRUG CONJUGATE". Page/Page column 55-56; 58-59. . Retrieved 2021/10/22.
• 2、 -. "PARA-AMINO-BENZYL LINKERS, PROCESS FOR THEIR PREPARATION AND THEIR USE IN CONJUGATES". Page/Page column 64-65. . Retrieved 2021/11/26.