O-BENZYL-L-SERINE

Base Information

• Chemical Name: O-BENZYL-L-SERINE
• CAS No.: 4726-96-9
• Molecular Formula: C10H13NO3
• Molecular Weight: 195.218
• Hs Code.: 29225090
• Mol file: 4726-96-9.mol

Synonyms:Alanine,3-(benzyloxy)-, L- (8CI);3-(Benzyloxy)-L-alanine;L-O-Benzylserine;O-(Phenylmethyl)-L-serine;O-Benzylserine;H-Ser(Bzl)-OH;

Chemical Property of O-BENZYL-L-SERINE

Chemical Property:

• Vapor Pressure: 8.83E-06mmHg at 25°C
• Melting Point: ~227 °C (dec.)
• Refractive Index: 7.3 ° (C=2, 1mol/L HCl)
• Boiling Point: 359.1 °C at 760 mmHg
• PKA: 2.10±0.10(Predicted)
• Flash Point: 170.9 °C
• PSA: 72.55000
• Density: 1.217 g/cm³
• LogP: 1.31540
• Storage Temp.: Store at RT.
• Solubility.: Aqueous Acid (Slightly), DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 195.08954328
• Heavy Atom Count: 14
• Complexity: 173

Purity/Quality:

98%,99%, ^*data from raw suppliers

O-Benzyl-L-Serine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COCC(C(=O)[O-])[NH3+]
• Isomeric SMILES: C1=CC=C(C=C1)COC[C@@H](C(=O)[O-])[NH3+]
• Uses: O-Benzyl-L-Serine is used in the preparation of serine analogs as specific agonists for NMDA receptor glycine binding sites. It also functions as an eluent for ligand exchange chromatography for the separation of constrained glutamate receptor ligands.

Technology Process of O-BENZYL-L-SERINE

There total 13 articles about O-BENZYL-L-SERINE 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: 100.0%

N-(4-Methoxybenzyloxycarbonyl)-O-benzyl-L-serine (4218-63-7) → O-Benzyl-L-serine (4726-96-9,32520-12-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 0.166667h;

DOI:10.1055/s-1989-27138

Reference yield: 97.0%

Z-Ser(Bzl)-OH (20806-43-3) → O-Benzyl-L-serine (4726-96-9,32520-12-0)

Guidance literature:

With ammonia; hydrogen; palladium on activated charcoal; In methanol; at 20 ℃;

DOI:10.1016/S0040-4020(98)00882-5

Reference yield: 62.3%

BOC-O-benzyl-L-serine (23680-31-1) → O-Benzyl-L-serine (4726-96-9,32520-12-0)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

upstream raw materials:

N-acetyl-O-benzyl-DL-serine

Z-Ser(Bzl)-OH

N-(4-Methoxybenzyloxycarbonyl)-O-benzyl-L-serine

O-Benzil-N-formil-(S)-(+)-serina

Downstream raw materials:

O-benzyl-L-serine methyl ester

[2-Benzyloxy-eth-(E)-ylidene]-(6-methoxy-1,4-dimethyl-9H-carbazol-3-ylmethyl)-amine

(S)-3-(benzyloxy)-2-((methoxycarbonyl)amino)propanoic acid

(-)-methyl (1S,2S,5S,6R)-3-benzyl-2exo-(benzyloxymethyl)-7,8-dioxa-3-azabicyclo[3.2.1]octane-6exo-carboxylate

Refernces

• 1、 Maolanon, Alex R.,Risgaard, Rune,Wang, Shuang-Yan,Snoep, Yoran,Papangelis, Athanasios,Yi, Feng,Holley, David,Barslund, Anne F.,Svenstrup, Niels,Hansen, Kasper B.,Clausen, Rasmus P.. "Subtype-Specific Agonists for NMDA Receptor Glycine Binding Sites". . p. 1681 - 1687. Retrieved 2017/08/21.
• 2、 Stuhr-Hansen, Nicolai,Padrah, Shahrokh,Str?mgaard, Kristian. "Facile synthesis of α-hydroxy carboxylic acids from the corresponding α-amino acids". supporting information. p. 4149 - 4151. Retrieved 2015/02/02.