128241-72-5

Basic information

• Product Name: D-AP3
• Synonyms: 3-PHOSPHONO-D-ALANINE;D-AP3;D(-)-2-AMINO-3-PHOSPHONOPROPANOIC ACID;D(-)-2-AMINO-3-PHOSPHONOPROPIONIC ACID;S(-)-2-AMINO-3-PHOSPHONOPROPIONIC ACID;(S)-(-)-2-Amino-3-phosphonopropionic acid, 3-Phosphono-D-alanine, D-AP3;(2S)-2-Amino-3-phosphonopropionic acid;(S)-2-Amino-3-phosphonopropanoic acid
• CAS NO: 128241-72-5
• Molecular Formula: C₃H₈NO₅P
• Molecular Weight: 169.07
• Mol File: 128241-72-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 224-226 °C(Solv: ethanol (64-17-5))
• Boiling Point: 481.6°Cat760mmHg
• Flash Point: 245.1°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 1.34E-10mmHg at 25°C
• Storage Temp.: 0-6°C
• PKA: 1.22±0.10(Predicted)
• CAS DataBase Reference: D-AP3(CAS DataBase Reference)
• NIST Chemistry Reference: D-AP3(128241-72-5)
• EPA Substance Registry System: D-AP3(128241-72-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 128241-72-5(Hazardous Substances Data)

Usage

Chemical Properties

white fine crystalline powder

InChI:InChI=1/C3H8NO5P/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)/p-2/t2-/m1/s1

Upstream product

• 86554-28-1 2-((S)-1-Phenyl-ethylamino)-3-phosphono-propionic acid 
• 909282-39-9 2(S)-amino-3-(diethoxyphosphoryl)propionic acid 
• 128164-60-3 (R)-methyl N-(tert-butoxycarbonyl)-2-amino-3-(dimethylphosphono)propanoate 

Relevant articles and documents

Enantioselective synthesis of (S)-2-amino-3-phosphonopropionic acid, (S)-AP-3, and (R)-2-amino-4-phosphonobutanoic acid, (R)-AP-4, via diastereoselective azidation of (4R,5R)-trans-N-[(diethoxyphosphoryl)propionyl]- and (4R,5R)-trans-N-[(diethoxyphosphoryl)butanoyl]hexahydrobenzoxazolidin-2-one

N-Acylation of readily available, enantiopure oxazolidinone (4R,5R)-1b with (diethoxyphosphoryl)propionyl chloride and (diethoxyphosphoryl)butanoyl chloride affords de title substrates (4R,5R)-2 and (4R,5R)-7, respectively, which are azidated with high diastereoselectivity by means of the reaction between their sodium enolates (4R,5R)-2-Na and (4R,5R)-7-Na with trisyl azide. Removal of the chiral auxiliary from azidated products (4R,5R,2′S)-3 and (4R,5R,2′R)-8 followed by hydrogenation and hydrolysis of the resulting carboxylic acids (S)-4 and (R)-9 gave the pharmacologically relevant aminophosphonic acids (S)-AP-3 and (R)-AP-4 in good yield.

PREPARATION D'ACIDES AMINOCARBOXY-ALKYLPHOSPHONIQUES OPTIQUEMENT ACTIFS

In aqueous solution ω-formylalkylphosphonates in the presence of hydrogen cyanide and (S) (-) α-methylbenzylamine give optically active aminonitriles with an enantiomeric excess of 50percent.Phosphonic aminonitriles are submitted to acid hydrolysis, then esterified and debenzylated without any epimerization.The separation is performed either with the acid or with the ester.All the operations are monitored by NMR (1H, 13C, 31P) and whenever possible, by GC.