(2R,4R)-2-amino-4-carbamoyl-4-fluorobutanoic acid

Base Information

• Chemical Name: (2R,4R)-2-amino-4-carbamoyl-4-fluorobutanoic acid
• CAS No.: 238418-69-4
• Molecular Formula: C₅H₉FN₂O₃
• Molecular Weight: 164.136
• Hs Code.: 2924190090
• DSSTox Substance ID: DTXSID801299781
• Mol file: 238418-69-4.mol

Synonyms:238418-69-4;(2R,4R)-2-amino-4-carbamoyl-4-fluorobutanoic acid;SCHEMBL12900723;DTXSID801299781;D-Glutamine, 4-fluoro-, (4R)-rel-;EN300-23906218

Chemical Property of (2R,4R)-2-amino-4-carbamoyl-4-fluorobutanoic acid

Chemical Property:

• Boiling Point: 462.5±45.0 °C(Predicted)
• PKA: 2.06±0.10(Predicted)
• PSA: 106.41000
• Density: 1.410±0.06 g/cm3(Predicted)
• LogP: 0.01240
• XLogP3: -3.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 164.05972032
• Heavy Atom Count: 11
• Complexity: 173

Purity/Quality:

99.90% ^*data from raw suppliers

DL-threo-4-Fluoroglutamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C(C(C(=O)O)N)C(C(=O)N)F
• Isomeric SMILES: C([C@H](C(=O)O)N)[C@H](C(=O)N)F
• Uses: DL-threo-4-Fluoroglutamine is the DL-threo diastereomer of 4-Fluoroglutamine, a fluorinated derivative of the essential amino acid, glutamine (G597000). 4-Fluoroglutamine was developed for in vivo positron emission tomography to aid in the understanding of the phenomenon of cancer cells strong requirement for glutamine.

Technology Process of (2R,4R)-2-amino-4-carbamoyl-4-fluorobutanoic acid

There total 10 articles about (2R,4R)-2-amino-4-carbamoyl-4-fluorobutanoic 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: 92.0%

(+/-)-erythro-Nα-(t-Butyloxycarbonyl)-4-fluoroglutamine → (+/-)-erythro-4-Fluoroglutamine (238418-69-4,238418-67-2)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 1h;

DOI:10.1016/S0022-1139(99)00188-8

Reference yield: 74.0%

(+/-)-threo-Nα-(t-Butyloxycarbonyl)-4-fluoroglutamine → (+/-)-threo-4-Fluoroglutamine (238418-69-4,238418-67-2)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 1h;

DOI:10.1016/S0022-1139(99)00188-8

Reference yield: 67.0%

(2S,4S)-tert-butyl-2-(tert-butoxycarbonylamino)-4-fluoro-5-oxo-5-(2,4,6-trimethoxybenzylamino)pentanoate (1262523-74-9) → (2S,4S)-2,5-diamino-4-fluoro-5-oxopentanoic acid (1262523-37-4,238418-69-4,238418-67-2)

Guidance literature:

With dimethylsulfide; trifluoroacetic acid; at 0 - 20 ℃;

DOI:10.1021/ja109203d

upstream raw materials:

erythro-4-fluoroglutamic acid 5-methyl ester

4-fluoroglutamic acid

(2S,4S)-tert-butyl-2-(tert-butoxycarbonylamino)-4-fluoro-5-oxo-5-(2,4,6-trimethoxybenzylamino)pentanoate