(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid

Base Information

• Chemical Name: (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS No.: 162558-25-0
• Molecular Formula: C23H26N2O6
• Molecular Weight: 426.469
• Hs Code.: 2924 29 70
• European Community (EC) Number: 871-379-5
• Nikkaji Number: J1.292.438K
• Mol file: 162558-25-0.mol

Synonyms:Fmoc-Dap(Boc)-OH;162558-25-0;Fmoc-Dapa(Boc)-OH;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;N-Fmoc-N'-Boc-L-2,3-Diaminopropionic acid;fmoc-alpha,beta-diaminopropionic acid(boc)-oh;MFCD00235896;(2S)-3-{[(tert-butoxy)carbonyl]amino}-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanoic acid;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)propanoic acid;Fmoc-L-Dap(Boc)-OH;Fmoc-L-2,3-Diaminopropionic acid(Boc);(S)-3-(tert-Butoxycarbonylamino)-2-[(9H-fluoren-9-ylmethoxy)carbonylamino]propionic Acid;(S)-3-(Boc-amino)-2-(Fmoc-amino)propionic Acid;SCHEMBL4600320;SCHEMBL12757436;3-(Boc-amino)-N-Fmoc-L-alanine;AKOS016842380;AC-8673;CS-W011638;AS-17628;AM20030098;B4174;B6107;Fmoc-Dap(Boc)-OH, >=97.0% (HPLC);Fmoc-3-(tert-Butyloxycarbonylamino)-L-Ala-OH;I10308;M03241;EN300-7363339;A810383;J-009950;Nbeta-Boc-Nalpha-Fmoc-L-2,3-diaminopropionic acid;Fmoc-(N-beta-Boc)-L-alpha,beta-diaminopropionic acid;Fmoc-Dapa(Boc)-OH (S)-3-(Boc-amino)-2-(Fmoc-amino)propionic acid;(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(tert-butoxycarbonylamino)propanoic acid;3-(tert-Butoxycarbonyl)amino-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine;L-Alanine, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-;N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-beta-t-butyloxycarbonyl-L-2,3-diaminopropionic acid

Chemical Property of (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 6.45E-18mmHg at 25°C
• Melting Point: 131-139 °C
• Refractive Index: 1.58
• Boiling Point: 652.5 °C at 760 mmHg
• PKA: 3.58±0.10(Predicted)
• Flash Point: 348.4 °C
• PSA: 113.96000
• Density: 1.263 g/cm³
• LogP: 4.28480
• Storage Temp.: 2-8°C
• Water Solubility.: Slightly soluble in water.
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 426.17908655
• Heavy Atom Count: 31
• Complexity: 639

Purity/Quality:

99% ^*data from raw suppliers

N-alpha-Fmoc-Nbeta-Boc-L-2,3-diaminopropionic acid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CC(C)(C)OC(=O)NC[C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Uses: As lysine residue its 3-amino group is often used for carrying a tag moiety such as a fluorescent dye, a quencher or biotin.

Technology Process of (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid

There total 15 articles about (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic 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: 72.0%

di-tert-butyl dicarbonate (24424-99-5) + 3-amino-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (181954-34-7) → N-α-tert-butoxycarbonyl-N-β-(9-fluorenylmethoxycarbonyl)-L-diaminopropionic acid (162558-25-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide; for 6h; Ambient temperature;

DOI:10.1016/S0040-4020(98)00354-8

Reference yield: 70.0%

(S)-3-(fluoren-9-ylmethoxycarbonyl)-4-[(tert-butyloxycarbonylamino)methyl]-5-oxazolidinone (918428-69-0) → N-α-tert-butoxycarbonyl-N-β-(9-fluorenylmethoxycarbonyl)-L-diaminopropionic acid (162558-25-0)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 20 ℃;

DOI:10.1080/00397910600772827

Reference yield: 67.0%

di-tert-butyl dicarbonate (24424-99-5) + N-(9-fluorenylmethoxylcarbonyl)-α,β-diaminopropionic acid hydrochloride (212688-53-4) → N-α-tert-butoxycarbonyl-N-β-(9-fluorenylmethoxycarbonyl)-L-diaminopropionic acid (162558-25-0)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 0 - 20 ℃; for 16h;

upstream raw materials:

di-tert-butyl dicarbonate

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

(S)-2-amino-3-((tert-butoxycarbonyl)amino)propanoic acid

3-amino-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

Downstream raw materials:

Fmoc-L-Dap(Boc)-OBn

C₄₂H₅₂N₁₀O₅

C₄₀H₄₈N₁₀O₅

C₄₀H₄₈N₁₀O₅

Refernces

• 1、 Hirschmann, Ralph,Yao, Wenqing,Arison, Byron,Maechler, Laurie,Rosegay, Avery,Sprengeler, Paul A.,Smith III, Amos B.. "Synthesis of the first tricyclic homodetic peptide. Use of coordinated orthogonal deprotection to achieve directed ring closure". . p. 7179 - 7202. Retrieved 1998.
• 2、 Ichikawa, Yoshiyasu,Ohara, Fumiyo,Kotsuki, Hiyoshizo,Nakano, Keiji. "A new approach to the neoglycopeptides: Synthesis of urea- and carbamate-tethered N-acetyl-D-glucosamine amino acid conjugates". . p. 5009 - 5012. Retrieved 2007/10/03.
• 3、 Akaji, Kenichi,Aimoto, Saburou. "Synthesis of MEN11420, a glycosylated bicyclic peptide, by intramolecular double cyclization using a chloroimidazolinium coupling reagent". . p. 1749 - 1755. Retrieved 2007/10/03.