5-tert-Butyl N-((9H-fluoren-9-ylmethoxy)carbonyl)-2-aminoglutarate

Base Information

• Chemical Name: 5-tert-Butyl N-((9H-fluoren-9-ylmethoxy)carbonyl)-2-aminoglutarate
• CAS No.: 71989-18-9
• Molecular Formula: C24H27NO6
• Molecular Weight: 425.481
• Hs Code.: 2924 29 70
• Mol file: 71989-18-9.mol

Synonyms:4-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoic acid;5-tert-Butyl N-((9H-fluoren-9-ylmethoxy)carbonyl)-2-aminoglutarate;MFCD00065648;MFCD00077054;N-Fmoc-D-glutamic Acid 1-(tert-Butyl) Ester;Fmoc-L-Glu(tBu)-OH*H2O;SCHEMBL5323666;BCP26020;Fmoc-Glu-OtBu;Fmoc-Glu(OBut)-OH;N-(9-Fluorenylmethyloxycarbonyl)-D-glutamic acid 1-tert-butyl ester;AKOS032947694;PD197327;SY021322;SY034169;N-Fmoc-L-glutamic Acid 1-tert-Butyl Ester;FT-0641979;FT-0658175;EN300-717884;A802083;5-(tert-butoxy)-4-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-5-oxopentanoic acid;205812-08-4

Chemical Property of 5-tert-Butyl N-((9H-fluoren-9-ylmethoxy)carbonyl)-2-aminoglutarate

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 3.72E-17mmHg at 25°C
• Melting Point: 83-90 °C
• Refractive Index: -4 ° (C=1, 80% AcOH)
• Boiling Point: 638.1 °C at 760 mmHg
• PKA: 3.70±0.10(Predicted)
• Flash Point: 339.7 °C
• PSA: 101.93000
• Density: 1.232 g/cm³
• LogP: 4.49110
• Storage Temp.: 2-8°C
• Solubility.: soluble in Methanol
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 425.18383758
• Heavy Atom Count: 31
• Complexity: 635

Purity/Quality:

≥98%, ^*data from raw suppliers

5-tert-Butyl N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-glutamate Hydrate >98.0%(HPLC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-27-36/37/39-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C(CCC(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Uses: Fmoc-Glu(OtBu)-OH (Fmoc-L-glutamic acid 5-tert-butyl ester) can be employed as a: Ligand in the synthesis of cis-substituted cyclopropane carboxylic acids via C-H activation of cyclopropane carboxamides using Pd catalyst.Linker in the preparation of multi-small molecule-conjugated PTX (paclitaxel) derivatives.It can be also used as a building block in the preparation of stapled α-helical peptides , and peptide C-terminal thioesters .

Technology Process of 5-tert-Butyl N-((9H-fluoren-9-ylmethoxy)carbonyl)-2-aminoglutarate

There total 10 articles about 5-tert-Butyl N-((9H-fluoren-9-ylmethoxy)carbonyl)-2-aminoglutarate 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: 91.0%

L-glutamic acid 5-tert-butyl ester (2419-56-9) + (9-fluorenyl)methyl pentafluorophenyl carbonate (88744-04-1) → Fmoc-Glu(OtBu)-OH (71989-18-9)

Guidance literature:

With sodium hydrogencarbonate; In water; acetone; Ambient temperature;

Reference yield: 87.0%

4-(1,1-dimethylethyl) ester of Nα-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamic acid allyl ester → Fmoc-Glu(OtBu)-OH (71989-18-9)

Guidance literature:

With [2-(dicyclohexylphosphino)ethyl]trimethylammonium chloride; phenylsilane; In tetrahydrofuran; water; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1055/s-0034-1378379

Reference yield: 87.0%

Fmoc-Glu(t-Bu)-1,1-dimethylallyl ester (851713-96-7) → Fmoc-Glu(OtBu)-OH (71989-18-9)

Guidance literature:

With 4-methyl-morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 25 ℃;

DOI:10.1021/ol0476117

upstream raw materials:

L-glutamic acid 5-tert-butyl ester

9-fluorenylmethyl N-succinimidyl carbonate

(9-fluorenyl)methyl pentafluorophenyl carbonate

L-glutamic acid

Downstream raw materials:

Fmoc-Glu(O-t-Bu)-ONp

Fmoc-Glu(OtBu)-OTDO

N^α-Fmoc-Glu-(O-tBu)-OPfp

(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-pentanedioic acid 5-tert-butyl ester 1-[4-(2,4-dichloro-phenoxycarbonylmethoxy)-benzyl] ester

Refernces

• 1、 Ankner, Tobias,Norberg, Thomas,Kihlberg, Jan. "Mild oxidative cleavage of 9-BBN-protected amino acid derivatives". . p. 3767 - 3770. Retrieved 2015/06/16.
• 2、 -. "Derivates of Polyethylene Glycol Modified Thymosin Alpha 1". . . Retrieved 2010/08/07.