| Identification | More | [Name]
N-Benzyloxycarbonyl-L-asparagine | [CAS]
2304-96-3 | [Synonyms]
4-AMINO-2-[[(BENZYLOXY)CARBONYL]AMINO]-4-OXOBUTANOIC ACID
BENZYLOXYCARBONYL-L-ASPARAGINE
CARBOBENZYLOXY-L-ASPARAGINE
CBZ-ASN-OH
CBZ-L-ASN
CBZ-L-ASPARAGINE
N2-[(PHENYLMETHOXY)CARBONYL]-L-ASPARAGINE
N-ALPHA-BENZYLOXYCARBONYL-L-ASPARAGINE
NALPHA-CARBOBENZOXY-L-ASPARAGINE
N-ALPHA-CARBOBENZYLOXY-L-ASPARAGINE
N(ALPHA)-CBZ-L-ASPARAGINE
N-BENZYLOXYCARBONYL-L-ASPARAGINE
N-CARBOBENZOXY-L-ASPARAGINE
N-CBZ-L-ASPARAGINE
N-CBZ-L-ASPARAGINE-OH
(S)-2-BENZYLOXYCARBONYLAMINO-SUCCINAMIC ACID
Z-ASN-OH
Z-ASPARAGINE
Z-L-ASN-OH
Z-L-ASPARAGINE | [EINECS(EC#)]
218-969-5 | [Molecular Formula]
C12H14N2O5 | [MDL Number]
MFCD00008035 | [Molecular Weight]
266.25 | [MOL File]
2304-96-3.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [Melting point ]
163-165 °C(lit.) | [alpha ]
6.5 º (c=2, CH3COOH) | [Boiling point ]
409.45°C (rough estimate) | [density ]
1.2846 (rough estimate) | [refractive index ]
6.3 ° (C=1.6, AcOH) | [storage temp. ]
0-6°C | [solubility ]
almost transparency in hot Methanol | [form ]
powder to crystal | [pka]
3.77±0.10(Predicted) | [color ]
White to Almost white | [Optical Rotation]
[α]20/D +6°, c = 1.6 in acetic acid | [BRN ]
3085452 | [InChIKey]
FUCKRCGERFLLHP-VIFPVBQESA-N | [CAS DataBase Reference]
2304-96-3(CAS DataBase Reference) | [EPA Substance Registry System]
2304-96-3(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,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 ]
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
| [Hazard Note ]
Irritant | [TSCA ]
Yes | [HazardClass ]
IRRITANT | [HS Code ]
29242990 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powde | [Uses]
Nα-Cbz-L-asparagine is an N-Cbz-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. | [Synthesis]
At 0 °C, 6.05 g (45 mmol) of L-asparagine was dissolved in 100 mL of 10% Na2CO3 aqueous solution, followed by the addition of 56 mL of 1,4-dioxane and 6.9 mL (40 mmol) of benzyl chloroformate. The reaction mixture was stirred overnight at room temperature and poured into 300 mL of water. The aqueous phase was extracted three times with ether. The aqueous phase was acidified with 2N HCl aqueous solution until a white precipitate precipitated. The precipitate was collected by filtration and washed well with ether to give Cbz-L-asparagine (Compound 14) as an off-white solid (9 g, 84% yield); Mass Spectra (ESI): m/z = 267 [M + H]+, 289 [M + Na]+. | [References]
[1] Tetrahedron Asymmetry, 2015, vol. 26, # 21-22, p. 1273 - 1280
[2] Tetrahedron, 2000, vol. 56, # 16, p. 2513 - 2522
[3] Tetrahedron Letters, 2015, vol. 56, # 26, p. 3999 - 4001
[4] European Journal of Organic Chemistry, 2014, vol. 2014, # 31, p. 7015 - 7022
[5] Chemical Communications, 2016, vol. 52, # 60, p. 9438 - 9441 |
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