(2R)-4-amino-2-azaniumyl-4-oxobutanoate

Base Information

• Chemical Name: (2R)-4-amino-2-azaniumyl-4-oxobutanoate
• CAS No.: 2058-58-4
• Molecular Formula: C4H8N2O3
• Molecular Weight: 132.119
• Hs Code.: 29241900
• Mol file: 2058-58-4.mol

Synonyms:D-asparagine zwitterion;CHEBI:74337;(2R)-4-amino-2-azaniumyl-4-oxobutanoate

Chemical Property of (2R)-4-amino-2-azaniumyl-4-oxobutanoate

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 2.38E-06mmHg at 25°C
• Melting Point: 280 °C (dec.)(lit.)
• Boiling Point: 438 °C at 760 mmHg
• PKA: 2.17(at 20℃)
• Flash Point: 218.7 °C
• PSA: 106.41000
• Density: 1.404 g/cm³
• LogP: -0.32570
• Storage Temp.: Store at 0-5°C
• XLogP3: -2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 132.05349212
• Heavy Atom Count: 9
• Complexity: 128

Purity/Quality:

99% ^*data from raw suppliers

D-Asparagine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C(C(=O)[O-])[NH3+])C(=O)N
• Isomeric SMILES: C([C@H](C(=O)[O-])[NH3+])C(=O)N

Technology Process of (2R)-4-amino-2-azaniumyl-4-oxobutanoate

There total 18 articles about (2R)-4-amino-2-azaniumyl-4-oxobutanoate 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: 18.6%

ASPARAGINE (3130-87-8,28088-48-4,7006-34-0) → (R)-Asparagine (2058-58-4,28088-48-4,7006-34-0)

Guidance literature:

With poly(4-vinyl pyridine) complex with L-glutamic acid; at 25 ℃; for 0.5h; Resolution of racemate;

DOI:10.1002/anie.202106603

Reference yield: 16.9%

ASPARAGINE (3130-87-8,28088-48-4,7006-34-0) → (R)-Asparagine (2058-58-4,28088-48-4,7006-34-0) + L-asparagine (70-47-3,28088-48-4,7006-34-0)

Guidance literature:

With copolymer of tri(ethylene glycol)-grafting polymethylsiloxane and poly(N⁶-methacryloyl-L-lysine); at 25 ℃; for 48h; Reagent/catalyst;

DOI:10.1002/anie.201803480

Reference yield:

→ ASPARAGINE (3130-87-8,28088-48-4,7006-34-0) + (R)-Asparagine (2058-58-4,28088-48-4,7006-34-0)

Guidance literature:

With ammonia; water; at 100 ℃; l-asparagine; Ein Gemisch gleicher Mengen l- und d-Asparagins entsteht;

upstream raw materials:

maleic anhydride

ASPARAGINE

L-asparagine

(R)-4-amino-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoic acid

Downstream raw materials:

N^α-[(2,4,5-trichloro-phenoxy)-acetyl]-D-asparagine

(2R)-aspartic acid

D-Malic acid

N-(2,4-Dichlor-phenoxyacetyl)-D-asparagin

Refernces

• 1、 Qie, Fengxiang,Guo, Jiahui,Tu, Bin,Zhao, Xing,Zhang, Yuchun,Yan, Yong. "β-Cyclodextrin Functionalized Nanoporous Graphene Oxides for Efficient Resolution of Asparagine Enantiomers". . p. 2812 - 2817. Retrieved 2018.
• 2、 Wan, Xinhua,Wang, Zhaoxu,Ye, Xichong,Zhang, Jie. "Noncovalently Functionalized Commodity Polymers as Tailor-Made Additives for Stereoselective Crystallization". supporting information. p. 20243 - 20248. Retrieved 2021/08/09.
• 3、 Wu, Peng,Wu, Yuping,Zhang, Junhui,Lu, Zhenyu,Zhang, Mei,Chen, Xuexian,Yuan, Liming. "Chromatographic Resolution of α-Amino Acids by (R)-(3,3'-Halogen Substituted-1,1'-binaphthyl)-20-crown-6 Stationary Phase in HPLC". supporting information. p. 1037 - 1042. Retrieved 2017/07/25.