Z-Asn-ome

Base Information

• Chemical Name: Z-Asn-ome
• CAS No.: 4668-37-5
• Molecular Formula: C13H16 N2 O5
• Molecular Weight: 280.28
• DSSTox Substance ID: DTXSID90426639
• Nikkaji Number: J1.819.067B
• Wikidata: Q82239496
• Mol file: 4668-37-5.mol

Synonyms:Z-ASN-OME;4668-37-5;methyl (2S)-4-amino-4-oxo-2-(phenylmethoxycarbonylamino)butanoate;Methyl N~2~-[(benzyloxy)carbonyl]-L-asparaginate;Z-L-asparagine methyl ester;SCHEMBL5181237;DTXSID90426639;MFCD02094371;AKOS027251026;FD21186;AS-48991;Methyl ((benzyloxy)carbonyl)-L-asparaginate;CS-0362731

Chemical Property of Z-Asn-ome

Chemical Property:

• PSA: 112.20000
• LogP: 1.68390
• Storage Temp.: -15°C
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 280.10592162
• Heavy Atom Count: 20
• Complexity: 353

Purity/Quality:

HPLC>98% ^*data from raw suppliers

N-α-Z-L-AsparagineMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CC(=O)N)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: COC(=O)[C@H](CC(=O)N)NC(=O)OCC1=CC=CC=C1

Technology Process of Z-Asn-ome

There total 10 articles about Z-Asn-ome 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: 99.0%

methanol (67-56-1) + N-benzyloxycarbonyl-L-asparagine (2304-96-3) → N-(benzyloxycarbonyl)asparagine methyl ester (4668-37-5)

Guidance literature:

With acetyl chloride; at -15 ℃;

DOI:10.1039/a808959k

Reference yield: 86.76%

1-methyl-1-nitrosourea (684-93-5) + N-benzyloxycarbonyl-L-asparagine (2304-96-3) → N-(benzyloxycarbonyl)asparagine methyl ester (4668-37-5)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; diethyl ether;

Reference yield: 62.0%

N-benzyloxycarbonyl-L-asparagine (2304-96-3) + methyl iodide (74-88-4) → N-(benzyloxycarbonyl)asparagine methyl ester (4668-37-5)

Guidance literature:

With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1021/ol3030583

upstream raw materials:

diazomethane

N-benzyloxycarbonyl-L-asparagine

methanol

Methyl formate

Downstream raw materials:

methyl-β-cyano-L-α-carbo benzoxyaminopropionate

(S)-methyl 3-amino-2-(((benzyloxy)carbonyl)amino)propanoate

(1-Ethyl-6-oxo-2-thioxo-hexahydro-pyrimidin-5-yl)-carbamic acid benzyl ester

methyl 3-benzyloxycarbonyl-2-oxo-imidazolidine-4(S)-carboxylate

Refernces

• 1、 Tahara, Yu-Ki,Ito, Mamoru,Kanyiva, Kyalo Stephen,Shibata, Takanori. "Total Synthesis of cis-Clavicipitic Acid from Asparagine via Ir-Catalyzed C-H bond Activation as a Key Step". . p. 11340 - 11343. Retrieved 2015/08/03.
• 2、 Angelici, Gaetano,Contaldi, Simone,Lynn Green, Sarah,Tomasini, Claudia. "Synthesis of imidazolidin-2-one-4-carboxylate and of (tetrahydro)pyrimidin- 2-one-5-carboxylate via an efficient modification of the Hofmann rearrangement". experimental part. p. 1849 - 1852. Retrieved 2008/10/09.