L-erythro-phenylserine

Base Information

• Chemical Name: L-erythro-phenylserine
• CAS No.: 7695-56-9
• Molecular Formula: C₉H₁₁NO₃
• Molecular Weight: 181.191
• Mol file: 7695-56-9.mol

Synonyms:L-erythro-phenylserine;L-erythro-3-phenylserine;L-erythro-beta-phenylserine

Chemical Property of L-erythro-phenylserine

Chemical Property:

• Vapor Pressure: 4.75E-07mmHg at 25°C
• Melting Point: 230-232 °C (decomp)
• Refractive Index: 1.609
• Boiling Point: 398 °C at 760 mmHg
• PKA: 2.06±0.10(Predicted)
• Flash Point: 194.5 °C
• PSA: 83.55000
• Density: 1.335 g/cm³
• LogP: 0.83220
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Sparingly), Water (Slightly, Heated)
• 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:

97% ^*data from raw suppliers

DL-threo-β-Phenylserine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C(C(=O)[O-])[NH3+])O
• Isomeric SMILES: C1=CC=C(C=C1)[C@H]([C@@H](C(=O)[O-])[NH3+])O

Technology Process of L-erythro-phenylserine

There total 33 articles about L-erythro-phenylserine 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:

N-acetyl-erythro-DL-β-phenylserine ethyl ester

(2RS,3RS)-2-amino-3-hydroxy-3-phenyl-propionic acid methyl ester; hydrochloride

erythro-DL-β-phenylserine ethyl ester hydrochloride

1-methyl-4-nitrosobenzene

Downstream raw materials:

(RS)-5-((RS)-α-hydroxy-benzyl)-imidazolidine-2,4-dione

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

benzaldehyde

glycine

Refernces

Synthesis of Oxazolidines, Thiazolidines, and 5,6,7,8-Tetrahydro-1H,3H-pyrrolo<1,2-c>oxazole (or thiazole)-1,3-diones from β-Hydroxy- or β-Mercapto-α-amino Acid Esters

10.1246/bcsj.54.1844

The study investigates the synthesis of oxazolidines, thiazolidines, and 5,6,7,8-tetrahydro-1H,3H-pyrrolo[1,2-c]oxazole (or thiazole)-1,3-diones from β-hydroxy- or β-mercapto-α-amino acid esters. Aromatic aldehydes such as benzaldehyde, p-anisaldehyde, p-chlorobenzaldehyde, and p-nitrobenzaldehyde are used to react with amino acid ethyl esters like L-serine, 3-phenyl-DL-serine, L-threonine, or L-cysteine to form oxazolidines or thiazolidines. These compounds can then be converted into oxazoles and thiazoles through dehydrogenation using N-bromosuccinimide. Acetylation of oxazolidines and thiazolidines leads to N-acetylderivatives, which can undergo cyclization in the presence of anhydrous ZnCl? to form the tetrahydro-pyrrolo[1,2-c]oxazole (or thiazole)-1,3-diones. The study also explores the interaction of oxazolidines and thiazolidines with p-nitrobenzaldehyde and piperidine to form Mannich bases. The IR spectra of the synthesized compounds are analyzed, showing characteristic shifts and absorptions related to functional groups such as the ester group and the oxazole or thiazole ring.

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