3-Fluoroglutamate

Base Information

• Chemical Name: 3-Fluoroglutamate
• CAS No.: 97315-76-9
• Molecular Formula: C₅H₈FNO₄
• Molecular Weight: 165.121
• Hs Code.: 2922499990
• DSSTox Substance ID: DTXSID80242865
• Wikidata: Q83126731
• Mol file: 97315-76-9.mol

Synonyms:3-fluoroglutamate;3-fluoroglutamate, threo-isomer;3-fluoroglutamic acid

Chemical Property of 3-Fluoroglutamate

Chemical Property:

• Vapor Pressure: 1.72E-06mmHg at 25°C
• Boiling Point: 370°Cat760mmHg
• Flash Point: 177.6°C
• PSA: 100.62000
• Density: 1.498g/cm³
• LogP: -0.08860
• XLogP3: -3.5
• 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:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 3-Fluoroglutamate

There total 4 articles about 3-Fluoroglutamate 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: 40.0%

D,L-erythro-N-acetyl-3-fluoroglutamic acid (19883-18-2,97413-77-9,97413-78-0) → (2R,3S)-3-fluoroglutamic acid (97315-76-9,142292-79-3,97550-60-2,97550-65-7) + D-erythro-3-fluoroglutamic acid (97550-59-9,142292-79-3,97550-60-2,97550-65-7)

Guidance literature:

In water; at 25 ℃; for 26h; acylase I, pH = 7;

DOI:10.1021/jo00217a029

Reference yield:

N-acetyl-3-hydroxyglutamic acid (97315-80-5,97315-81-6) → (2R,3S)-3-fluoroglutamic acid (97315-76-9,142292-79-3,97550-60-2,97550-65-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.540 g / hydrogen fluoride, sulfur tetrafluoride / 1 h / -78 °C

2: 40 percent / H₂O / 26 h / 25 °C / acylase I, pH = 7

With sulfur tetrafluoride; hydrogen fluoride; In water;

DOI:10.1021/jo00217a029

Reference yield:

diethyl 2-oxo-3-carbetoxy-3-fluoroglutarate (1608-58-8) → (2R,3S)-3-fluoroglutamic acid (97315-76-9,142292-79-3,97550-60-2,97550-65-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) CH₃COOH, HCl / 1.) RT, 3 d, 2.) 50 deg C, 5 h

2: ethanol / 72 h / 30 °C / EDTA, NAD⁽¹⁺⁾, bovine serum albumin, GLDH, YADH, ammonium phosphate buffer (pH 7)

With hydrogenchloride; acetic acid; In ethanol;

DOI:10.1021/jo00263a048

upstream raw materials:

disodium 2-oxo-3-fluoroglutarate

D,L-erythro-N-acetyl-3-fluoroglutamic acid

N-acetyl-3-hydroxyglutamic acid

diethyl 2-oxo-3-carbetoxy-3-fluoroglutarate

Downstream raw materials:

methyl trans-3-fluoro-5-ketopyrrolidine-2-carboxylate

Refernces

• 1、 Vidal-Cros, Anne,Gaudry, Michel,Marquet, Andree. "L-threo- and L-erythro-3-Fluoroglutamic Acids. Synthesis by Fluorodehydroxylation and Enzymatic Resolution.". . p. 3163 - 3167. Retrieved 2007/10/02.