Boc-Asn-ONp

Base Information

• Chemical Name: Boc-Asn-ONp
• CAS No.: 4587-33-1
• Molecular Formula: C15H19N3O7
• Molecular Weight: 353.332
• Hs Code.: 29242990
• European Community (EC) Number: 685-351-3
• DSSTox Substance ID: DTXSID30884092
• Nikkaji Number: J421.729B
• Wikidata: Q27105953
• Mol file: 4587-33-1.mol

Synonyms:Boc-Asn-ONp;4587-33-1;(S)-4-Nitrophenyl 4-amino-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate;Boc-Asn-OPhNO2;Boc-L-asparagine 4-nitrophenyl ester;L-Asparagine, N2-((1,1-dimethylethoxy)carbonyl)-, 4-nitrophenyl ester;(4-nitrophenyl) (2S)-4-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoate;L-Asparagine, N2-[(1,1-dimethylethoxy)carbonyl]-, 4-nitrophenyl ester;MFCD00056109;Nalpha-Boc-L-asparagine 4-nitrophenyl ester;Nalpha-(tert-Butoxycarbonyl)-L-asparagine 4-Nitrophenyl Ester;CHEBI:3147;SCHEMBL7417267;N2-((1,1-Dimethylethoxy)carbonyl)-L-asparagine, 4-nitrophenyl ester;DTXSID30884092;C15H19N3O7;AKOS015889942;AM81566;CS-W011853;FD21160;HY-W011137;Boc-Asn-ONp, >=98.0% (HPLC);AS-48980;N-|A-Boc-L-asparagine 4-nitrophenyl ester;B3915;C02138;Q27105953;N-alpha-t-Butyloxycarbonyl-L-asparagine p-nitrophenyl ester

Chemical Property of Boc-Asn-ONp

Chemical Property:

• Vapor Pressure: 8.7E-15mmHg at 25°C
• Melting Point: 116-118 °C(lit.)
• Refractive Index: 1.55
• Boiling Point: 609.3 °C at 760 mmHg
• PKA: 10.57±0.46(Predicted)
• Flash Point: 322.3 °C
• PSA: 153.54000
• Density: 1.318 g/cm³
• LogP: 2.88330
• Storage Temp.: 2-8°C
• Solubility.: slightly sol. in Methanol
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 353.12229995
• Heavy Atom Count: 25
• Complexity: 516

Purity/Quality:

99% ^*data from raw suppliers

Na-Boc-L-asparagine 4-nitrophenyl ester 98+% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC(=O)N)C(=O)OC1=CC=C(C=C1)[N+](=O)[O-]
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC(=O)N)C(=O)OC1=CC=C(C=C1)[N+](=O)[O-]
• Uses: Boc-Asn-ONp, is an Asparagine derivative used in peptide chemistry.

Technology Process of Boc-Asn-ONp

There total 4 articles about Boc-Asn-ONp 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: 90.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + N-tert-butyloxycarbonylasparagine (7536-55-2) → N-(tert-butyloxycarbonyl)-L-asparagine p-nitrophenyl ester (4587-33-1)

Guidance literature:

With dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide;

DOI:10.1134/S1068162009060120

Reference yield:

tert-butyl fluoroformate (18595-34-1) → N-(tert-butyloxycarbonyl)-L-asparagine p-nitrophenyl ester (4587-33-1)

Guidance literature:

Multi-step reaction with 2 steps

1: dioxane; H₂O

2: DCC / tetrahydrofuran; dimethylformamide

With dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide;

Reference yield:

tert-Butyl 4-nitrophenyl carbonate (13303-10-1) → N-(tert-butyloxycarbonyl)-L-asparagine p-nitrophenyl ester (4587-33-1)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N

2: DCC

With triethylamine; dicyclohexyl-carbodiimide;

DOI:10.1002/hlca.19630460518

upstream raw materials:

4-nitro-phenol

N-tert-butyloxycarbonylasparagine

tert-butyl fluoroformate

tert-Butyl 4-nitrophenyl carbonate

Downstream raw materials:

Benzoic acid (R)-2-((S)-2-tert-butoxycarbonylamino-3-carbamoyl-propionylamino)-1-carboxy-ethyl ester

(S)-N-tert-butyl-3-[(2S,3S)-3-[(S)-2-(tert-butoxycarbonyl)aminosuccinamyl]amino-2-hydroxy-4-phenylbutanoyl]pyrrolidine-2-carboxamide

(R)-N-tert-butyl-3-[(2S,3S)-3-[(S)-2-(tert-butoxycarbonyl)aminosuccinamyl]amino-2-hydroxy-4-phenylbutanoyl]-1,3-thiazolidine-4-carboxamide

(R)-N-tert-butyl-3-[(2S,3S)-3-[(S)-2-(tert-butoxycarbonyl)aminosuccinamyl]amino-2-hydroxy-4-phenylbutanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide

Refernces

• 1、 -. "Peptides correlated to lysozyme". . . Retrieved 2008/06/13.