CID 16219489

Base Information

• Chemical Name: CID 16219489
• CAS No.: 103404-90-6
• Molecular Formula: C₅H₆O₅*2Na
• Molecular Weight: 192.079
• Hs Code.: 29181990
• Mol file: 103404-90-6.mol

Synonyms:

Chemical Property of CID 16219489

Chemical Property:

• Melting Point: >291°C (dec.)
• PSA: 100.49000
• LogP: -3.37270
• Storage Temp.: −20°C
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 171.02694263
• Heavy Atom Count: 11
• Complexity: 141

Purity/Quality:

98%,99%, ^*data from raw suppliers

(2R)-2-HydroxyglutaricAcidDisodiumSalt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(CC(=O)O)C(C(=O)O)O.[Na]
• Isomeric SMILES: C(CC(=O)O)[C@H](C(=O)O)O.[Na]
• Description: D-α-Hydroxyglutaric Acid (D-2-HG) is an α-hydroxy acid that is over-produced in the human neurometabolic disease D-2-hydroxyglutaric aciduria (D-2-HGA). It is normally synthesized from 2-ketoglutarate (2-KG) by hydroxyacid-oxoacid transhydrogenase (HOT), although defects in HOT are not known to be associated with D-2-HGA. Instead, type I D-2-HGA involves mutations in D-2-hydroxyglutarate dehydrogenase, which converts D-2-HG back to 2-KG. Type II D-2-HGA results from gain-of-function mutations in isocitrate dehydrogenase 2, causing it to supplement HOT in converting 2-KG to D-2-HG. In bacteria, this α-hydroxy acid may be synthesized from oxalate and propionyl-coenzyme A by an α-hydroxyglutaric acid synthetase.
• Uses: A potential inhibitor of glutamate carboxypeptidase.

Technology Process of CID 16219489

There total 2 articles about CID 16219489 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: 62.0%

L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → (S)-2-hydroxypentanedioic acid, disodium salt (40951-21-1,55714-86-8,63512-50-5,103404-90-6)

Guidance literature:

L-glutamic acid; With potassium nitrite; sulfuric acid; In water; at -10 ℃;

With sodium hydroxide; Further stages.;

DOI:10.1002/hlca.200790195

Reference yield: 31.43%

(2S)-tetrahydro-5-oxofuran-2-carboxylic acid (21461-84-7) → (S)-2-hydroxypentanedioic acid, disodium salt (40951-21-1,55714-86-8,63512-50-5,103404-90-6)

Guidance literature:

With sodium hydroxide; In water; at 25 ℃; for 2h; pH=10;

DOI:10.7717/peerj.9438

Reference yield: 77.0%

4-nitrobenzyl chloride (100-14-1) + (S)-2-hydroxypentanedioic acid, disodium salt (40951-21-1,55714-86-8,63512-50-5,103404-90-6) → bis(4-nitrobenzyl) 2-hydroxypentanedioate

Guidance literature:

In N,N-dimethyl-formamide; at 120 ℃; for 6h;

DOI:10.1002/hlca.200790195

upstream raw materials:

L-glutamic acid

(2S)-tetrahydro-5-oxofuran-2-carboxylic acid

Downstream raw materials:

(S)-dimethyl 2-hydroxypentanedioate

(R)-5-Oxo-tetrahydro-furan-2-carboxylic acid 4-bromo-phenyl ester

(R)-2-(2-Nitro-benzoyloxy)-pentanedioic acid dimethyl ester

(R)-2-(2,6-Dinitro-benzoyloxy)-pentanedioic acid dimethyl ester

Refernces

• 1、 Heizmann, Gerhard,Pfleiderer, Wolfgang. "Pteridines Part CXVIII. Methanopterin, chemical approach and partial synthesis". . p. 1856 - 1873. Retrieved 2008/03/12.