tert-Butoxycarbonylasparagine

Base Information

• Chemical Name: tert-Butoxycarbonylasparagine
• CAS No.: 7536-55-2
• Molecular Formula: C9H16N2O5
• Molecular Weight: 232.236
• Hs Code.: 2924 19 00
• European Community (EC) Number: 231-405-2
• DSSTox Substance ID: DTXSID80884401
• Nikkaji Number: J307.866C
• Wikidata: Q27105952
• ChEMBL ID: CHEMBL1222167
• Mol file: 7536-55-2.mol

Synonyms:Boc-Asn-OH;7536-55-2;Boc-L-asparagine;tert-Butoxycarbonylasparagine;Boc-Asn;N-(tert-Butoxycarbonyl)-L-asparagine;Nalpha-Boc-L-asparagine;tert-Butoxycarbonyl-L-asparagine;N-(tert-Butoxycarbonyl)asparagine;tert-Butyloxycarbonyl-L-asparagine;N-alpha-Boc-L-asparagine;N(a)-tert-Butoxycarbonyl-L-asparagine;N(2)-tert-Butoxycarbonyl-L-asparagine;N-alpha-t-BOC-L-ASPARAGINE;MFCD00038152;N2-((1,1-Dimethylethoxy)carbonyl)-L-asparagine;Boc-L-Asn-OH;L-Asparagine, N2-[(1,1-dimethylethoxy)carbonyl]-;Asparagine, N(2)-carboxy-, N(2)-tert-butyl ester, L-;CHEBI:3146;C9H16N2O5;EINECS 231-405-2;NSC 154980;N(alpha)-t-butoxycarbonyl-L-asparagine;2-tert-Butoxycarbonylamino-succinamic acid;L-Asparagine, N2-((1,1-dimethylethoxy)carbonyl)-;BOC-(S)-2-AMINOSUCCINIC ACID 4-AMIDE MONOHYDRATE;(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-carbamoylpropanoic acid;Nalpha-(tert-Butoxycarbonyl)-L-asparagine;N2-((tert-Butoxy)carbonyl)-L-asparagine;N2-[(tert-butoxy)carbonyl]-L-asparagine;BOC-ASPARAGINE;N2-[(1,1-Dimethylethoxy)carbonyl]-L-asparagine;N-BOC-L-ASPARAGINE;BocAsnOH;Boc- Asn-OH;N-a-t-Boc-asparagine;N-A-BOC-L-ASPARAGINE;SCHEMBL607848;CHEMBL1222167;DTXSID80884401;N-tert-butoxycarbonyl-L-asparagine;(tert-Butoxycarbonyl)-L-asparagine;N-tert-butyloxycarbonyl-L-asparagine;STL466184;(2S)-4-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoic acid;AKOS012536057;AKOS015922890;Na-(tert-Butoxycarbonyl)-L-asparagine;AC-8608;Boc-Asn-OH, >=98.5% (T);CS-W019494;N-T-BUTOXYCARBONYL-L-ASPARAGINE;DS-13747;N(2)-(tert-butoxycarbonyl)-L-asparagine;N~2~-(tert-butoxycarbonyl)-L-asparagine;SY024209;AM20100735;B1627;C01410;EN300-186646;M03264;N-[(1,1-dimethylethoxy)carbonyl]-L-asparagine;N-ALPHA-T-BUTYLOXYCARBONYL-L-ASPARAGINE;J-300046;Q-101639;L-Asparagine, N(2)-[(1,1-dimethylethoxy)carbonyl]-;Q27105952;(S)-4-AMINO-2-(TERT-BUTOXYCARBONYLAMINO)-4-OXOBUTANOIC ACID

Chemical Property of tert-Butoxycarbonylasparagine

Chemical Property:

• Appearance/Colour: White amorphous powder
• Vapor Pressure: 1.33E-10mmHg at 25°C
• Melting Point: 175 °C (dec.)(lit.)
• Refractive Index: -7 ° (C=1, DMF)
• Boiling Point: 481.7 °C at 760 mmHg
• PKA: 3.79±0.10(Predicted)
• Flash Point: 245.1 °C
• PSA: 118.72000
• Density: 1.253 g/cm³
• LogP: 0.93090
• Storage Temp.: −20°C
• Solubility.: almost transparency in N,N-DMF
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 232.10592162
• Heavy Atom Count: 16
• Complexity: 295

Purity/Quality:

98% ^*data from raw suppliers

N-alpha- ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC(=O)N)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC(=O)N)C(=O)O
• Uses: Nα-Boc-L-asparagine is an N-Boc-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 tert-Butoxycarbonylasparagine

There total 18 articles about tert-Butoxycarbonylasparagine 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: 91.0%

L-asparagine (70-47-3,28088-48-4,7006-34-0) + di-tert-butyl dicarbonate (24424-99-5) → N-tert-butyloxycarbonylasparagine (7536-55-2)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 20 ℃;

Reference yield: 84.0%

(R)-Asparagine (2058-58-4,28088-48-4,7006-34-0) + di-tert-butyl dicarbonate (24424-99-5) → N-t-butyloxycarbonyl-D-asparagine (7536-55-2,142847-17-4,75647-01-7)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 20 ℃;

Reference yield: 80.0%

(R)-Asparagine (2058-58-4,28088-48-4,7006-34-0) → N-t-butyloxycarbonyl-D-asparagine (7536-55-2,142847-17-4,75647-01-7)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; for 20h; Ambient temperature;

DOI:10.1016/S0040-4020(01)87142-8

upstream raw materials:

N-(tert-butyloxycarbonyl) azide

L-asparagine

tert-butyl fluoroformate

di-tert-butyl dicarbonate

Downstream raw materials:

N'-Boc-L-argininate ethyl ester

{(S)-1-[(S)-5-Benzoylamino-1-((1S,2R)-1-carbamoyl-2-hydroxy-propylcarbamoyl)-pentylcarbamoyl]-2-carbamoyl-ethyl}-carbamic acid tert-butyl ester

2-(tert-butoxycarbonyl)amino-3-cyanopropanoic acid

N^α-(tert-butoxycarbonyl)-(S)-asparagine methyl ester

Refernces

• 1、 Franz, M. Heiko,Iorga, Mirela,Maftei, Catalin V.,Maftei, Elena,Neda, Ion. "Studies on the constituents of Helleborus purpurascens: use of derivatives from calix[6]arene, homooxacalix[3]arene and homoazacalix[3]arene as extractant agents for amino acids from the aqueous extract". . p. 55 - 72. Retrieved 2019/12/30.
• 2、 -. "Improvement of methods for synthesizing dencichine". Paragraph 0010; 0011; 0018. . Retrieved 2019/05/28.