N-Benzyloxycarbonyl-L-asparagine Chemical Properties

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. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

almost transparency in hot Methanol

form 

powder to crystal

pka

3.77±0.10(Predicted)

color 

White to Almost white

optical activity

[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

L-Asparagine, N2-[(phenylmethoxy)carbonyl]- (2304-96-3)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

24/25-36-26

WGK Germany 

3

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29242990

MSDS

• Language:English Provider:4-Amino-2-{[(benzyloxy)carbonyl]amino}-4-oxobutanoic acid
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

N-Benzyloxycarbonyl-L-asparagine Usage And Synthesis

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

N-Benzyloxycarbonyl-L-asparagine(2304-96-3)Related Product Information

• Diethylstilbestrol
• Glycine
• CARBONYL SULFIDE
• Trimethoprim
• PYRAZOPHOS
• 1,1'-Carbonyldiimidazole
• D-(-)-Asparagine monohydrate
• L-Asparagine
• ASPARAGINASE
• tert-Butyl carbazate
• N-Carbobenzyloxyglycine
• 6-Aminocaproic acid
• FMOC-ASN(TRT)-OPFP
• Z-ASN-ONP
• Z-ASP-OME
• N-Cbz-L-Aspartic acid 4-tert-butyl ester
• Z-ASN(TRT)-OH
• Z-ARG(NO2)-OH