N-Cbz-D-Asparagine

Base Information

• Chemical Name: N-Cbz-D-Asparagine
• CAS No.: 4474-86-6
• Molecular Formula: C12H14N2O5
• Molecular Weight: 266.254
• Hs Code.: 29225090
• DSSTox Substance ID: DTXSID30364824
• Nikkaji Number: J208.196B
• Wikidata: Q63392931
• Mol file: 4474-86-6.mol

Synonyms:N-Cbz-D-Asparagine;4474-86-6;Z-D-Asn-OH;Nalpha-Cbz-D-asparagine;N-CARBOBENZOXY-D-ASPARAGINE;CBZ D-Asparagine;D-Asparagine, N2-[(phenylmethoxy)carbonyl]-;(2R)-4-amino-4-oxo-2-(phenylmethoxycarbonylamino)butanoic acid;C12H14N2O5;Carbobenzoxy-L-asparagine;MFCD00065696;(2R)-2-{[(benzyloxy)carbonyl]amino}-3-carbamoylpropanoic acid;SCHEMBL3569541;Nalpha-Carbobenzoxy-D-asparagine;FUCKRCGERFLLHP-SECBINFHSA-;DTXSID30364824;((Benzyloxy)carbonyl)-D-asparagine;AKOS016842396;Nalpha -Benzyloxycarbonyl-D-asparagine;AS-16060;2(R)-benzyloxycarbonylamino-succinamic acid;CS-0149990;C-2105;EN300-121308;A826678;J-300052;Q63392931;(2R)-4-Amino-2-(benzyloxycarbonylamino)-4-oxo-butanoic acid;(R)-4-amino-2-[[(benzyloxy)carbonyl]amino]-4-oxobutanoic acid;(R)-4-AMINO-2-(BENZYLOXYCARBONYLAMINO)-4-OXOBUTANOIC ACID;(2R)-4-azanyl-4-oxidanylidene-2-(phenylmethoxycarbonylamino)butanoic acid

Chemical Property of N-Cbz-D-Asparagine

Chemical Property:

• Appearance/Colour: White to off white powder
• Melting Point: 162-164 °C
• Refractive Index: -6.5 ° (C=1.6, AcOH)
• Boiling Point: 580.6 °C at 760 mmHg
• Flash Point: 304.9 °C
• PSA: 118.72000
• Density: 1.355 g/cm³
• LogP: 1.33260
• Storage Temp.: Store at RT.
• Solubility.: almost transparency in hot Methanol
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 266.09027155
• Heavy Atom Count: 19
• Complexity: 339

Purity/Quality:

99% ^*data from raw suppliers

Z-D-Asn ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NC(CC(=O)N)C(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)N[C@H](CC(=O)N)C(=O)O
• Uses: Nα-Cbz-D-asparagine is an N-Cbz-protected form of D-Asparagine (A788960). D-Asparagine is an isomer of L-Asparagine (A790005) and is used by bacteria (such as Saccharomyces cerevisiae) as a sole nitrogen source for replication. L-Asparagine is also a competitive inhibitor of staphylococcal L-asparaginase and is used as a reagent to synthesize peptide antibiotics.

Technology Process of N-Cbz-D-Asparagine

There total 6 articles about N-Cbz-D-Asparagine 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: 85.0%

N-Benzyloxycarbonyl-D-asparagin-p-nitrobenzylester (3561-56-6,58578-32-8) → 2-Benzyloxycarbonylamino-succinamic acid (2304-96-3,4474-86-6,29880-22-6)

Guidance literature:

With sodium dithionite; sodium carbonate; In acetonitrile;

Reference yield:

N-benzyloxy-carbonyl-DL-asparagine (29880-22-6) → (R)-4-amino-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoic acid (4474-86-6) + N-benzyloxycarbonyl-L-asparagine (2304-96-3)

Guidance literature:

resolved on CSP cellulose tris(3,5-dimethylphenylcarbamate) by chiral HPLC;

DOI:10.1246/cl.1988.1125

Reference yield:

(R)-Asparagine (2058-58-4,28088-48-4,7006-34-0) + benzyl chloroformate (501-53-1,94274-21-2) → (R)-4-amino-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoic acid (4474-86-6)

Guidance literature:

DOI:10.1021/jo00126a002

upstream raw materials:

N-benzyloxy-carbonyl-DL-asparagine

(R)-Asparagine

benzyl chloroformate

L-asparagine monohydrate

Downstream raw materials:

N²-acetyl-D-asparagine

2-(R)-amino>-3-aminopropionic acid

(S)-2-oxo-imidazolidine-1,5-dicarboxylic acid 1-benzyl ester

(S)‐2‐oxoimidazolidine‐1,5‐dicarboxylate-5‐tert‐butyl ester-1‐benzyl ester

Refernces

• 1、 Khayer, Khurshida,Jenn, Thierry,Akhtar, Mahmoud,John, Robert,Gani, David. "Synthesis of (R)- and (S)-2,3-diaminopropyl sulfate: Mechanism based inhibition of glutamate 1-semialdehyde aminomutase". . p. 1637 - 1641. Retrieved 2007/10/03.
• 2、 Gudasheva, T. A.,Rozantsev, G. G.,Ostrovskaya, R. U.,Trofimov, S. S.,Voronina, T. A.,et al.. "SYNTHESIS OF PYROGLUTAMYLASPARAGINE AMIDE DIPEPTIDE FRAGMENT OF VASOPRESSIN, AND THE STEREOSELECTIVITY OF ITS MNEMIC EFFECT". . p. 14 - 17. Retrieved 2007/10/03.