Ethyl N2-((benzyloxy)carbonyl)-L-asparaginate

Base Information

• Chemical Name: Ethyl N2-((benzyloxy)carbonyl)-L-asparaginate
• CAS No.: 4668-38-6
• Molecular Formula: C₁₄H₁₈N₂O₅
• Molecular Weight: 294.307
• European Community (EC) Number: 225-113-4
• DSSTox Substance ID: DTXSID50196902
• Nikkaji Number: J297.879B
• Wikidata: Q83069883
• Mol file: 4668-38-6.mol

Synonyms:4668-38-6;Z-ASN-OET;Ethyl N2-((benzyloxy)carbonyl)-L-asparaginate;(S)-Ethyl 4-amino-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoate;EINECS 225-113-4;ethyl (2S)-4-amino-4-oxo-2-(phenylmethoxycarbonylamino)butanoate;ethyl N2-[(benzyloxy)carbonyl]-L-asparaginate;SCHEMBL7742003;DTXSID50196902;ethyl ((benzyloxy)carbonyl)-L-asparaginate;(S)-ethyl 4-amino-2-(benzyloxycarbonylamino)-4-oxobutanoate;(S)-Ethyl4-amino-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoate

Chemical Property of Ethyl N2-((benzyloxy)carbonyl)-L-asparaginate

Chemical Property:

• Vapor Pressure: 8.17E-12mmHg at 25°C
• Boiling Point: 542.1°Cat760mmHg
• Flash Point: 281.6°C
• PSA: 107.72000
• Density: 1.235g/cm³
• LogP: 1.81110
• Storage Temp.: 2-8°C
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 294.12157168
• Heavy Atom Count: 21
• Complexity: 366

Purity/Quality:

99% ^*data from raw suppliers

ethyl((benzyloxy)carbonyl)-L-asparaginate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Ethyl N2-((benzyloxy)carbonyl)-L-asparaginate

There total 3 articles about Ethyl N2-((benzyloxy)carbonyl)-L-asparaginate 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: 79.0%

ethanol (64-17-5) + N-benzyloxy-carbonyl-DL-asparagine (29880-22-6) → N-benzyloxycarbonyl-D,L-asparagine ethyl ester (126401-11-4,4668-38-6)

Guidance literature:

With thionyl chloride;

DOI:10.1016/j.tet.2003.10.118

Reference yield: 50.0%

N-benzyloxycarbonyl-D,L-asparagine ethyl ester (126401-11-4,4668-38-6) → N-benzyloxycarbonyl-D-asparagine methyl ester (160348-02-7) + N-benzyloxycarbonyl-D-asparagine ethyl ester (4668-38-6)

Guidance literature:

With sodium hydroxide; savinase 16L; sodium chloride; In tetrahydrofuran; phosphate buffer; for 17h; pH=6.5;

DOI:10.1016/j.tet.2003.10.118

Reference yield:

N-benzyloxy-carbonyl-DL-asparagine (29880-22-6) → N-benzyloxycarbonyl-D-asparagine ethyl ester (4668-38-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / SOCl₂

2: 50 percent / Savinase 16L; NaCl; NaOH / aq. phosphate buffer; tetrahydrofuran / 17 h / pH 6.5

With sodium hydroxide; thionyl chloride; savinase 16L; sodium chloride; In tetrahydrofuran; phosphate buffer;

DOI:10.1016/j.tet.2003.10.118

upstream raw materials:

ethanol

N-benzyloxy-carbonyl-DL-asparagine

N-benzyloxycarbonyl-D,L-asparagine ethyl ester

Downstream raw materials:

(R)-(1-benzyl-2,5-dioxo-pyrrolidin-3-yl)carbamic acid benzyl ester

(S)-(1-benzyl-2,5-dioxo-pyrrolidin-3-yl)carbamic acid benzyl ester

Refernces