L-Glutamic acid 5-tert-butyl ester

Base Information

• Chemical Name: L-Glutamic acid 5-tert-butyl ester
• CAS No.: 2419-56-9
• Molecular Formula: C9H17NO4
• Molecular Weight: 203.238
• Hs Code.: 29224999
• DSSTox Substance ID: DTXSID70426672
• Nikkaji Number: J1.896.982C
• Mol file: 2419-56-9.mol

Synonyms:H-Glu(OtBu)-OH;2419-56-9;L-Glutamic acid 5-tert-butyl ester;(S)-2-Amino-5-(tert-butoxy)-5-oxopentanoic acid;(2S)-2-amino-5-(tert-butoxy)-5-oxopentanoic acid;5-tert-Butyl L-Glutamate;(2S)-2-amino-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoic acid;H-Glu(O-t-Bu)-OH;MFCD00038580;Glu(OtBu);Glu(tBu);(2S)-2-Amino-5-tert-butoxy-5-oxopentanoic acid;SCHEMBL130831;l-glutamic acid 5-t-butyl ester;DTXSID70426672;Glutamic acid 5-tert-butyl ester;OIOAKXPMBIZAHL-LURJTMIESA-N;AC-482;NSC823865;STL466179;AKOS005175152;CS-W015458;FD21428;HY-W014742;NSC-823865;AS-12202;PD196954;B4045;BB 0261763;EN300-198996;(S)-2-amino-5-tert-butoxy-5-oxopentanoic acid;A817140;J-015390;J-521644;L-Glutamic acid 5-tert-butyl ester, >=98.0% (TLC);(2S)-2-amino-5-tert-butoxy-5-oxopentanoic acid (non-preferred name);(2S)-2-azanyl-5-[(2-methylpropan-2-yl)oxy]-5-oxidanylidene-pentanoic acid;Glutamic acid gamma-t-butyl ester (H-Glu(OtBu)-OH) (H-L-Glu(tBu)-OH)

Chemical Property of L-Glutamic acid 5-tert-butyl ester

Chemical Property:

• Vapor Pressure: 2.11E-05mmHg at 25°C
• Melting Point: 182°C(lit.)
• Refractive Index: 1.475
• Boiling Point: 336.4 °C at 760 mmHg
• PKA: 2.20±0.10(Predicted)
• Flash Point: 157.3 °C
• PSA: 89.62000
• Density: 1.133 g/cm³
• LogP: 1.22050
• Storage Temp.: 2-8°C
• Water Solubility.: Sparingly soluble in water; practically insoluble in ethanol or ether.
• XLogP3: -2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 203.11575802
• Heavy Atom Count: 14
• Complexity: 219

Purity/Quality:

99% ^*data from raw suppliers

L-Glutamic Acid 5-tert-Butyl Ester ^*data from reagent suppliers

Safty Information:

• Statements: 22-24
• Safety Statements: 22-24/25-25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)CCC(C(=O)O)N
• Isomeric SMILES: CC(C)(C)OC(=O)CC[C@@H](C(=O)O)N
• Uses: L-Glutamic acid 5-tert-butyl ester is used as a fine chemical intermediate, pharmaceutical intermediate.

Technology Process of L-Glutamic acid 5-tert-butyl ester

There total 18 articles about L-Glutamic acid 5-tert-butyl ester 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: 96.0%

5-tert-butyl N-benzyloxycarbonyl-L-glutamate (3886-08-6) → L-glutamic acid 5-tert-butyl ester (2419-56-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 24h; under 760 Torr;

DOI:10.1002/1522-2675(200205)85:5<1210::AID-HLCA1210>3.0.CO;2-T

Reference yield: 92.0%

Fmoc-Glu(OtBu)-OH (71989-18-9) → L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) + L-glutamic acid 5-tert-butyl ester (2419-56-9)

Guidance literature:

Fmoc-Glu(OtBu)-OH; With sodium azide; In N,N-dimethyl-formamide; at 50 ℃; for 4h;

With piperidine; In N,N-dimethyl-formamide;

DOI:10.1007/s00726-013-1625-7

Reference yield: 50.0%

di-tert-butyl L-glutamate (16874-06-9) → L-glutamic acid 5-tert-butyl ester (2419-56-9)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 1.5h; Enzymatic reaction;

DOI:10.1021/op0341115

upstream raw materials:

5-tert-butyl N-benzyloxycarbonyl-L-glutamate

H-Glu(O-t-Bu)-OBzl

N-(2-)-propyl-(2)-oxycarbonyl)-glutaminsaeure-γ-tert.-butylester

(S)-2-Benzyloxycarbonylamino-pentanedioic acid 1-benzyl ester 5-tert-butyl ester

Downstream raw materials:

N--L-glutaminsaeure-γ-tert.-butylester

Cbz-Ile-Glu(OtBu)-Ala-OH

Cbz-Ile-Glu(OtBu)-OSuc

2-azido-pentanedioic acid 5-tert-butyl ester

Refernces

• 1、 -. "ANTI-CD40 ANTIBODY DRUG CONJUGATES". Paragraph 00149. . Retrieved 2019/06/17.
• 2、 Hymel, David,Cai, Sutang,Sun, Qi,Henkhaus, Rebecca S.,Perera, Chamani,Peterson, Blake R.. "Fluorescent mimics of cholesterol that rapidly bind surfaces of living mammalian cells". supporting information. p. 14624 - 14627. Retrieved 2015/09/28.