Carbobenzoxy-L-asparagine

Base Information

• Chemical Name: Carbobenzoxy-L-asparagine
• CAS No.: 2304-96-3
• Deprecated CAS: 35264-96-1
• Molecular Formula: C12H14N2O5
• Molecular Weight: 266.254
• Hs Code.: 29242990
• European Community (EC) Number: 218-969-5
• DSSTox Substance ID: DTXSID90883824
• Nikkaji Number: J36.784B
• Wikidata: Q72441937
• Mol file: 2304-96-3.mol

Synonyms:benzyloxycarbonyl-asparagine;benzyloxycarbonylasparagine;Z-Asp

Chemical Property of Carbobenzoxy-L-asparagine

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 2.54E-14mmHg at 25°C
• Melting Point: 160-165 °C
• Refractive Index: 6.3 ° (C=1.6, AcOH)
• Boiling Point: 580.6 °C at 760 mmHg
• PKA: 3.77±0.10(Predicted)
• Flash Point: 304.9 °C
• PSA: 118.72000
• Density: 1.355 g/cm³
• LogP: 1.33260
• Storage Temp.: 0-6°C
• Solubility.: almost transparency in hot Methanol
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 266.09027155
• Heavy Atom Count: 19
• Complexity: 339

Purity/Quality:

99% ^*data from raw suppliers

Nα-Cbz-L-asparagine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NC(CC(=O)N)C(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)N[C@@H](CC(=O)N)C(=O)O
• Uses: Nα-Cbz-L-asparagine is an N-Cbz-protected form of L-Asparagine (A790005). L-Asparagine was first isolated by Robiquet and Vauquelin from asparagus juice (a high source of L-asparagine). L-Asparagine is often incorporated into proteins, and is a basis for some cancer therapies as certain cancerous cells require L-asparagine for growth.

Technology Process of Carbobenzoxy-L-asparagine

There total 19 articles about Carbobenzoxy-L-asparagine 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: 98.0%

(S)-N-benzyloxycarbonylaspargine t-butyl ester (25456-85-3) → N-benzyloxycarbonyl-L-asparagine (2304-96-3)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In dichloromethane; for 0.583333h; Ambient temperature;

DOI:10.1016/S0040-4039(00)79116-7

Reference yield: 95.0%

L-asparagine (70-47-3,28088-48-4,7006-34-0) + dimethylsulfonium methyl sulfate → N-benzyloxycarbonyl-L-asparagine (2304-96-3)

Guidance literature:

With triethylamine; In water; Ambient temperature;

DOI:10.1246/bcsj.62.3103

Reference yield: 85.0%

N-Benzyloxycarbonyl-D-asparagin-p-nitrobenzylester (3561-56-6,58578-32-8) → 2-Benzyloxycarbonylamino-succinamic acid (2304-96-3,4474-86-6,29880-22-6)

Guidance literature:

With sodium dithionite; sodium carbonate; In acetonitrile;

upstream raw materials:

L-asparagine

Z-Asp(OBzl)-OH

N-benzyloxy-carbonyl-DL-asparagine

benzyl chloroformate

Downstream raw materials:

N²-benzyloxycarbonyl-N⁴-xanthen-9-yl-L-asparagine

N-benzyloxycarbonyl-L-asparagine p-nitrophenyl ester

(N-Benzyloxycarbonyl-L-asparagin)-(4-nitro-benzylester)

Z-Asn-OSu

Refernces

• 1、 -. "Method for synthesizing chiral 4-(N-carbobenzoxy) pyrrolidone". Paragraph 0021-0024. . Retrieved 2019/10/01.
• 2、 Ghosh, Subrata K.,Ganzmann, Carola,Gladysz, John A.. "Synthesis of a series of ω-dimethylaminoalkyl substituted ethylenediamine ligands for use in enantioselective catalysis". . p. 1273 - 1280. Retrieved 2015/11/09.