5-Phosphono-D-norvaline

Base Information

• Chemical Name: 5-Phosphono-D-norvaline
• CAS No.: 79055-68-8
• Molecular Formula: C₅H₁₂NO₅P
• Molecular Weight: 197.128
• European Community (EC) Number: 622-112-4,635-985-1
• UNII: CD39X2NL7F
• DSSTox Substance ID: DTXSID201000239
• Nikkaji Number: J264.539D
• Wikipedia: AP5
• Wikidata: Q209309
• ChEMBL ID: CHEMBL84612
• Mol file: 79055-68-8.mol

Synonyms:2 Amino 5 phosphonopentanoate;2 Amino 5 phosphonopentanoic Acid;2 Amino 5 phosphonovalerate;2 Amino 5 phosphonovaleric Acid;2-Amino-5-phosphonopentanoate;2-Amino-5-phosphonopentanoic Acid;2-Amino-5-phosphonovalerate;2-Amino-5-phosphonovaleric Acid;2-APV;5 Phosphononorvaline;5-Phosphononorvaline;d-APV;dl-APV

Chemical Property of 5-Phosphono-D-norvaline

Chemical Property:

• Appearance/Colour: white fine crystalline powder
• Vapor Pressure: 1.28E-10mmHg at 25°C
• Melting Point: approximate 233℃
• Boiling Point: 482.1 °C at 760 mmHg
• PKA: 2.46±0.10(Predicted)
• Flash Point: 245.4 °C
• PSA: 130.66000
• Density: 1.529 g/cm³
• LogP: 0.05650
• Storage Temp.: Store at RT
• Sensitive.: Light Sensitive
• Solubility.: Soluble to 100 mM in sterile
• XLogP3: -5.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 197.04530948
• Heavy Atom Count: 12
• Complexity: 200

Purity/Quality:

99% ^*data from raw suppliers

EIF4G2 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(CC(C(=O)O)N)CP(=O)(O)O
• Isomeric SMILES: C(C[C@H](C(=O)O)N)CP(=O)(O)O
• Description: D-AP5 is a selective N-methyl-D-aspartate (NMDA) receptor antagonist (Kd = 1.4 μM) that competitively inhibits the glutamate binding site of NMDA receptors. Whereas D-AP5 is the active (?)-stereoisomer, its (+)-isomer (L-AP5) demonstrates considerably less potent NMDA receptor antagonist activity. AP5 has been widely used to study the activity of NMDA receptors particularly in regard to researching synaptic plasticity, learning, and memory.
• Uses: A competitive NMDA antagonist

Technology Process of 5-Phosphono-D-norvaline

There total 10 articles about 5-Phosphono-D-norvaline 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: 81.0%

(-)-(2R,3E)-2-amino-5-phosphono-3-pentenoic acid (118492-04-9) → AP-5 (76326-31-3,76726-92-6,79055-67-7,79055-68-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 3h; under 760 Torr; Ambient temperature;

DOI:10.1271/bbb.60.680

Reference yield: 65.0%

(R)-2-Amino-5-(diethoxy-phosphoryl)-pentanoic acid → AP-5 (76326-31-3,76726-92-6,79055-67-7,79055-68-8)

Guidance literature:

With hydrogenchloride; pyrographite; Heating;

Reference yield: 54.0%

(E)-N-(2-hydroxy-2-phenyleth-1-yl)-5-phosphonopent-4-enoic acid hydrochloride → AP-5 (76326-31-3,76726-92-6,79055-67-7,79055-68-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In water; at 55 ℃; under 3102.9 Torr;

DOI:10.1021/jo00270a045

upstream raw materials:

(-)-(2R,3E)-2-amino-5-phosphono-3-pentenoic acid

(E)-3-(3-(diethylphosphono)prop-2-en-1-yl)-4-(tert-butoxycarbonyl)-5-phenyl-2H-1,4-oxazin-2-one

(R)-tert-butyl 4-(3-(diethoxyphosphoryl)propyl)-2,2-dimethyloxazolidine-3-carboxylate

APV

Refernces

• 1、 Fukuari, Masashi,Ichimoto, Itsuo,Kirihata, Mitsunori. "Asymmetric synthesis of D-(E)-2-amino-5-phosphono-3-pentenoic acid (APPA) by using a chiral auxiliary". . p. 680 - 682. Retrieved 2007/10/03.
• 2、 Garcia-Barradas, Oscar,Juaristi, Eusebio. "Highly enantioselective synthesis of (R)- and (S)-2-amino-5-phosphonopentanoic acids [(R)- and (S)-AP5] via modified Seebach imidazolidinones". . p. 3423 - 3434. Retrieved 2007/10/02.