(2S,3R)-2-azaniumyl-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoate

Base Information

• Chemical Name: (2S,3R)-2-azaniumyl-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoate
• CAS No.: 3916-18-5
• Molecular Formula: C₉H₁₁NO₅
• Molecular Weight: 213.19
• Pharos Ligand ID: R9GN68J12MVK
• Metabolomics Workbench ID: 149711
• Mol file: 3916-18-5.mol

Synonyms:

Chemical Property of (2S,3R)-2-azaniumyl-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoate

Chemical Property:

• Vapor Pressure: 6.39E-13mmHg at 25°C
• Melting Point: >200oC
• Refractive Index: 1.692
• Boiling Point: 549.8 °C at 760 mmHg
• PKA: 2.09±0.24(Predicted)
• Flash Point: 286.3 °C
• PSA: 124.01000
• Density: 1.608 g/cm³
• LogP: 0.24340
• Storage Temp.: -15°C
• Solubility.: ethanol: 50 mg/mL Solutions should be freshly prepared.
• XLogP3: -3.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 213.06372245
• Heavy Atom Count: 15
• Complexity: 229

Purity/Quality:

99% ^*data from raw suppliers

DL-threo-Droxidopa ^*data from reagent suppliers

Safty Information:

• Safety Statements: S24/25:Avoid contact with skin and eyes.

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C(C(C(=O)[O-])[NH3+])O)O)O
• Isomeric SMILES: C1=CC(=C(C=C1[C@H]([C@@H](C(=O)[O-])[NH3+])O)O)O
• Uses: A synthetic amino acid precursor of Norepinephrine. Antiparkinsonian.

Technology Process of (2S,3R)-2-azaniumyl-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoate

There total 6 articles about (2S,3R)-2-azaniumyl-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoate 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:

3,4-dibenzyloxybenzaldehyde (5447-02-9) → (+/-)-threo-DOPS (492-46-6,3916-18-5,6204-89-3,13147-26-7,16322-99-9,23651-95-8,34047-62-6,34124-73-7,50731-20-9,51829-98-2,51829-99-3,89886-54-4)

Guidance literature:

Multi-step reaction with 2 steps

1: aq.-ethanolic NaOH / anschliessendes Erwaermen mit wss. HCl

2: palladium; aqueous methanol / Hydrogenation

With methanol; sodium hydroxide; palladium;

Reference yield:

D,L-threo-3-(3,4-Dibenzyloxyphenyl)serine (55449-18-8,55449-19-9,55637-52-0,70543-77-0,70561-66-9,106887-48-3,113139-65-4,124709-63-3,146985-69-5) → (+/-)-threo-DOPS (492-46-6,3916-18-5,6204-89-3,13147-26-7,16322-99-9,23651-95-8,34047-62-6,34124-73-7,50731-20-9,51829-98-2,51829-99-3,89886-54-4)

Guidance literature:

With methanol; palladium; Hydrogenation;

Reference yield:

(2RS:3SR)-2-amino-3-hydroxy-3-(3,4-bis-ethoxycarbonyloxy-phenyl)-propionic acid ethyl ester → (+/-)-threo-DOPS (492-46-6,3916-18-5,6204-89-3,13147-26-7,16322-99-9,23651-95-8,34047-62-6,34124-73-7,50731-20-9,51829-98-2,51829-99-3,89886-54-4)

Guidance literature:

With alkaline solution;

upstream raw materials:

D,L-threo-3-(3,4-Dibenzyloxyphenyl)serine

3,4-dibenzyloxybenzaldehyde

3,4-bis(ethoxycarboxy)-benzaldehyde

(2RS.3RS)-2-amino-3-(3,4-bis-benzyloxy-phenyl)-3-hydroxy-propionic acid