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N-Benzyloxycarbonyl-L-asparagine

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CAS:2304-96-3
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N-Benzyloxycarbonyl-L-asparagine Basic information
Product Name:N-Benzyloxycarbonyl-L-asparagine
Synonyms:n2-[(phenylmethoxy)carbonyl]-l-asparagin;L-Asparagine, N-CBZ protected;N-α-Z-L-asparagine;N(a)-Benzyloxycarbonyl-L-asparagine;N-A-CBZ-L-ASPARAGINE CRYSTALLINE;N2-[(PHENYLMEHTOXY)CARBONYL]-L-ASPARAGINE;CBZ-L-Asparagine-OH;N(alpha)-Benzyloxycarbonyl-L-asparagine~Z-Asn-OH
CAS:2304-96-3
MF:C12H14N2O5
MW:266.25
EINECS:218-969-5
Product Categories:Z-Amino acid series;Chiral Compounds;Amino Acids;Amino Acids (N-Protected);Biochemistry;Cbz-Amino Acids;Asparagine [Asn, N];Z-Amino Acids and Derivatives;chiral;Amino Acid Derivatives;PROTECTED AMINO ACID & PEPTIDES;Alkyl;Asparagine;Building Blocks;Chemical Biology;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks;Peptide Chemistry;ADVANCED INT.
Mol File:2304-96-3.mol
N-Benzyloxycarbonyl-L-asparagine Structure
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
pka3.77±0.10(Predicted)
form powder to crystal
color White to Almost white
Optical Rotation[α]20/D +6°, c = 1.6 in acetic acid
BRN 3085452
InChIKeyFUCKRCGERFLLHP-VIFPVBQESA-N
CAS DataBase Reference2304-96-3(CAS DataBase Reference)
EPA Substance Registry SystemL-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 TSCA listed
HazardClass IRRITANT
HS Code 29242990
MSDS Information
ProviderLanguage
4-Amino-2-{[(benzyloxy)carbonyl]amino}-4-oxobutanoic acid English
ACROS English
SigmaAldrich English
ALFA English
N-Benzyloxycarbonyl-L-asparagine Usage And Synthesis
Chemical Propertieswhite to light yellow crystal powde
UsesNα-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
L-Asparagine

70-47-3

Benzyl chloroformate

501-53-1

N-Benzyloxycarbonyl-L-asparagine

2304-96-3

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 Preparation Products And Raw materials
Raw materialsL-Asparagine-->Benzyl chloroformate-->1,4-Dioxane-->Sodium carbonate
Preparation ProductsZ-ASN-GLY-OH-->(S)-3-N-CBZ-AMINO-SUCCINIMIDE -->Z-ASN-ONP
Tag:N-Benzyloxycarbonyl-L-asparagine(2304-96-3) Related Product Information
Diethylstilbestrol 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 Glycine Z-ASN(TRT)-OH Z-ARG(NO2)-OH