(2R,4S)-2-amino-4-fluoropentanedioic acid

Base Information

• Chemical Name: (2R,4S)-2-amino-4-fluoropentanedioic acid
• CAS No.: 132746-47-5
• Molecular Formula: C5H8FNO4
• Molecular Weight: 165.1197232
• DSSTox Substance ID: DTXSID80426486
• Nikkaji Number: J1.253.263F
• Wikidata: Q82239391
• Mol file: 132746-47-5.mol

Synonyms:132746-47-5;(2R,4S)-2-amino-4-fluoropentanedioic acid;D-Glutamic acid, 4-fluoro-, (4S)- (9CI);DL-erythro-4-Fluoroglutamic acid;AC1OCXLX;91383-48-1;SCHEMBL5704713;D-erythro-4-Fluoroglutamic acid;DTXSID80426486;MFCD00153160;(2R,4S)-2-Amino-4-fluoroglutaric acid

Chemical Property of (2R,4S)-2-amino-4-fluoropentanedioic acid

Chemical Property:

• PSA: 100.62000
• LogP: -0.08860
• XLogP3: -3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 165.04373590
• Heavy Atom Count: 11
• Complexity: 172

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C(C(C(=O)O)N)C(C(=O)O)F
• Isomeric SMILES: C([C@H](C(=O)O)N)[C@@H](C(=O)O)F

Technology Process of (2R,4S)-2-amino-4-fluoropentanedioic acid

There total 5 articles about (2R,4S)-2-amino-4-fluoropentanedioic 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: 100.0%

D,L-erythro,threo-4-fluoroglutamic acid (2708-77-2,149117-03-3,91383-48-1,91383-47-0) → (+/-)-2-Fluoro-4-aminobutanoic acid (5130-17-6,34069-57-3) + (-)-D-erythro-4-fluoroglutamic acid (132746-47-5,149117-03-3,91383-48-1,91383-47-0) + d-threo-(2R,4R)-4-Fluoroglutamic acid (149117-03-3,91383-48-1,91383-47-0)

Guidance literature:

With sodium hydroxide; glutamic decarboxylase ex Escherichia coli; pyridoxal 5'-phosphate; In pyridine; water; at 30 ℃; for 48h;

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

Reference yield: 75.0%

(+/-)-erythro-4-Fluoroglutamic acid (149117-03-3,91383-48-1,91383-47-0) → (-)-D-erythro-4-fluoroglutamic acid (132746-47-5,149117-03-3,91383-48-1,91383-47-0) + (R)-4-Amino-2-fluorobutyric acid (34069-57-3)

Guidance literature:

With sodium hydroxide; glutamic decarboxylase ex Escherichia coli; pyridoxal 5'-phosphate; In pyridine; water; at 30 ℃; for 24h;

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

Reference yield: 55.0%

Methyl 1-acetyl-trans-4-fluoro-D-pyrrolidin-5-one-2-carboxylate (149033-38-5) → (-)-D-erythro-4-fluoroglutamic acid (132746-47-5,149117-03-3,91383-48-1,91383-47-0)

Guidance literature:

With hydrogenchloride; for 4h; Heating;

DOI:10.1016/S0040-4039(00)88500-7

upstream raw materials:

Methyl 1-acetyl-trans-4-fluoro-D-pyrrolidin-5-one-2-carboxylate

D,L-erythro,threo-4-fluoroglutamic acid

(+/-)-erythro-4-Fluoroglutamic acid

(2S,4S)-1-acetyl-4-hydroxyproline methyl ester

Downstream raw materials:

(+/-)-2-Fluoro-4-aminobutanoic acid

Refernces

• 1、 Tolman, Vladimír,Sedmera, Petr. "Chemistry of 4-fluoroglutamic acid. Part 3. Preparation of the diastereomers of 4-fluoroglutamine and 4-fluoroisoglutamine. An enzymatic access to the antipodes of 4-amino-2-fluorobutyric acid". . p. 5 - 10. Retrieved 2000.