| Identification | More | [Name]
BOC-L-Asparagine | [CAS]
7536-55-2 | [Synonyms]
BOC-ASN
BOC-ASN-OH
BOC-ASPARAGINE
BOC-L-ASN
BOC-L-ASN-OH
BOC-L-ASPARAGINE
BOC-L-ASPARAGINE-OH
N2-[(1,1-Dimethylethoxy)carbonyl]-L-asparagine
NALPHA-BOC-L-ASPARAGINE
N-ALPHA-T-BOC-L-ASPARAGINE
N-ALPHA-T-BUTOXYCARBONYL-L-ASPARAGINE
N-(ALPHA)-TERT-BUTOXYCARBONYL-L-ASPARAGINE
N-ALPHA-TERT-BUTYLOXYCARBONYL-L-ASPARAGINE
N-BOC-L-ASPARAGINE
N-T-BOC-L-ASPARAGINE
N-T-BUTOXYCARBONYL-L-ASPARAGINE
N-TERT-BUTOXYCARBONYL-L-ASPARAGINE
TBOC-L-ASPARAGINE
T-BUTYLOXYCARBONYL-L-ASPARAGINE
n2-[(1,1-dimethylethoxy)carbonyl]-l-asparagin | [EINECS(EC#)]
231-405-2 | [Molecular Formula]
C9H16N2O5 | [MDL Number]
MFCD00038152 | [Molecular Weight]
232.23 | [MOL File]
7536-55-2.mol |
| Chemical Properties | Back Directory | [Appearance]
WHITE AMORPHOUS POWDER | [Melting point ]
175 °C (dec.)(lit.)
| [Boiling point ]
374.39°C (rough estimate) | [density ]
1.2896 (rough estimate) | [refractive index ]
-7 ° (C=1, DMF) | [Fp ]
245°C | [storage temp. ]
−20°C
| [solubility ]
almost transparency in N,N-DMF | [form ]
Powder or Crystalline Powder | [pka]
3.79±0.10(Predicted) | [color ]
White | [Optical Rotation]
[α]20/D 7.8±0.5°, c = 2% in DMF | [Detection Methods]
T,NMR,Rotation | [BRN ]
1977963 | [Major Application]
peptide synthesis | [InChI]
InChI=1S/C9H16N2O5/c1-9(2,3)16-8(15)11-5(7(13)14)4-6(10)12/h5H,4H2,1-3H3,(H2,10,12)(H,11,15)(H,13,14)/t5-/m0/s1 | [InChIKey]
FYYSQDHBALBGHX-YFKPBYRVSA-N | [SMILES]
C(O)(=O)[C@H](CC(N)=O)NC(OC(C)(C)C)=O | [CAS DataBase Reference]
7536-55-2(CAS DataBase Reference) | [EPA Substance Registry System]
7536-55-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [TSCA ]
Yes | [HazardClass ]
IRRITANT | [HS Code ]
29241990 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Chemical Properties]
WHITE AMORPHOUS POWDER | [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. | [Definition]
ChEBI: The Nalpha-t-butoxycarbonyl derivative of L-asparagine | [reaction suitability]
reaction type: Boc solid-phase peptide synthesis | [Synthesis]
L-asparagine (15 g, 0.113 mol, 1.0 eq.) and sodium carbonate (12 g, 0.113 mol, 1.0 eq.) were dissolved in a solvent mixture of water (225 mL) and 1,4-dioxane (225 mL) at room temperature. To this solution was slowly added di-tert-butyl dicarbonate (30 g, 0.137 mol, 1.2 eq.) and the reaction mixture was stirred overnight at room temperature. Upon completion of the reaction, 1,4-dioxane was removed by distillation under reduced pressure. Subsequently, the pH of the solution was adjusted to 2 with 37% hydrochloric acid, at which point a white solid precipitated. The solid product was collected by filtration, washed with water and dried under appropriate conditions. Finally, 24 g of BOC-L-asparagine was obtained in 91% yield. The product characterization data were as follows: melting point 175°C-180°C (literature value 175°C); 1H NMR (DMSO-D6) δ 12.5 (1H, br); 7.31 (1H, br); 6.91 (1H, br); 6.87 (1H, d, J=8.4 Hz); 4.23 (1H, q, J=7.7 Hz); 2.56- 2.36 (2H, m); 1.38 (9H, s). | [References]
[1] Patent: WO2005/21558, 2005, A2. Location in patent: Page/Page column 214
[2] Patent: US2006/189806, 2006, A1. Location in patent: Page/Page column 38
[3] Bioorganic and Medicinal Chemistry, 1998, vol. 6, # 8, p. 1185 - 1208
[4] Angewandte Chemie - International Edition, 2007, vol. 46, # 14, p. 2470 - 2477
[5] Organic Syntheses, 1985, vol. 63, p. 160 - 160 |
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