2-Azaniumyl-3-hydroxy-3-phenylpropanoate

Base Information

• Chemical Name: 2-Azaniumyl-3-hydroxy-3-phenylpropanoate
• CAS No.: 69-96-5
• Molecular Formula: C9H11 N O3
• Molecular Weight: 181.191
• Mol file: 69-96-5.mol

Synonyms:

Chemical Property of 2-Azaniumyl-3-hydroxy-3-phenylpropanoate

Chemical Property:

• Vapor Pressure: 3.8E-10mmHg at 25°C
• Melting Point: 202-208 °C (dec.)
• Boiling Point: 483.1oC at 760 mmHg
• Flash Point: 246oC
• PSA: 83.55000
• Density: 1.335
• LogP: 0.83220
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 181.07389321
• Heavy Atom Count: 13
• Complexity: 172

Purity/Quality:

98%min ^*data from raw suppliers

DL-beta-Phenylserine, threo form ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C(C(=O)[O-])[NH3+])O
• Uses: DL-beta-Phenylserine, threo form is used in the enantioselective synthesis of cyclic pentapeptides. This compound also showed analgesic activity in mice when the mice were pretreated with pargyline.

Technology Process of 2-Azaniumyl-3-hydroxy-3-phenylpropanoate

There total 51 articles about 2-Azaniumyl-3-hydroxy-3-phenylpropanoate 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: 94.0%

(2S,3R)-2-Dibenzylamino-3-hydroxy-3-phenyl-propionic acid (118965-98-3,118966-02-2) → dl-threo-phenylserine (69-96-5,1078-17-7,2584-74-9,2584-75-0,6254-48-4,7352-06-9,7687-36-7,7695-56-9,32946-42-2,50897-27-3,68296-26-4,109120-55-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1016/S0040-4020(01)85997-4

Reference yield: 90.0%

C6H9NO4 (153547-44-5,182267-22-7,256386-82-0) → dl-threo-phenylserine (69-96-5,1078-17-7,2584-74-9,2584-75-0,6254-48-4,7352-06-9,7687-36-7,7695-56-9,32946-42-2,50897-27-3,68296-26-4,109120-55-0)

Guidance literature:

With lithium hydroxide; In water; at 20 ℃; for 2h;

DOI:10.1021/ol991225l

Reference yield: 51.5%

benzaldehyde (100-52-7) + glycine (56-40-6,18875-39-3,25718-94-9) → dl-threo-phenylserine (69-96-5,1078-17-7,2584-74-9,2584-75-0,6254-48-4,7352-06-9,7687-36-7,7695-56-9,32946-42-2,50897-27-3,68296-26-4,109120-55-0)

Guidance literature:

With sodium hydroxide; at 0 - 20 ℃; for 1.5h;

DOI:10.1248/cpb.51.1363

upstream raw materials:

benzaldehyde

glycine

2-Dibenzylamino-3-hydroxy-3-phenyl-propionic acid

ethyl N-benzylideneglycinate

Downstream raw materials:

2-(2-chloro-acetylamino)-3-hydroxy-3-phenyl-propionic acid

(2RS,3RS)-2-(2-chloro-acetylamino)-3-hydroxy-3-phenyl-propionic acid

(2RS,3SR)-2-(2-chloro-acetylamino)-3-hydroxy-3-phenyl-propionic acid

(2RS,3RS)-2-amino-3-hydroxy-3-phenyl-propionic acid

Refernces

• 1、 Shee, Prakash K.,Ratnayake, Nishanka Dilini,Walter, Tyler,Goethe, Olivia,Onyeozili, Edith Ndubuaku,Walker, Kevin D.. "Exploring the scope of an α/β-aminomutase for the amination of cinnamate epoxides to arylserines and arylisoserines". . p. 7418 - 7430. Retrieved 2019/08/20.
• 2、 -. "A PRODUCING METHOD OF D-FORM OR L-FORM AMINO ACID DERIVATIVES HAVING A THIOL GROUP". Paragraph 0174; 0175. . Retrieved 2016/10/31.