N~2~-[(benzyloxy)carbonyl]glutamine

Base Information

• Chemical Name: N~2~-[(benzyloxy)carbonyl]glutamine
• CAS No.: 2650-64-8
• Molecular Formula: C13H16N2O5
• Molecular Weight: 280.28
• Hs Code.: 29242990
• NSC Number: 186903
• ChEMBL ID: CHEMBL1161938
• Mol file: 2650-64-8.mol

Synonyms:N~2~-[(benzyloxy)carbonyl]glutamine;50516-14-8;N2-[(benzyloxy)carbonyl]glutamine;2-{[(benzyloxy)carbonyl]amino}-4-carbamoylbutanoic acid;Carbobenzoxy-L-glutamine;5-Amino-2-(((benzyloxy)carbonyl)amino)-5-oxopentanoic acid;5-Amino-2-[[(benzyloxy)carbonyl]amino]-5-oxopentanoic acid;Carbobenzyloxy-L-glutamine;N-(Benzyloxycarbonyl)-L-glutamine;MFCD00008043;MFCD00065698;N.alpha.-Benzyloxycarbonyl-L-glutamine;Nalpha-Cbz-D-glutamine;N-alpha-Z-L-glutamine;DL-Glutamine, N2-[(phenylmethoxy)carbonyl]-;SCHEMBL716988;CHEMBL1161938;5-amino-5-oxo-2-(phenylmethoxycarbonylamino)pentanoic acid;Glutamine, N2-benzyl ester, L-;JIMLDJNLXLMGLX-UHFFFAOYSA-N;NSC186903;STL466717;AKOS000201439;AKOS016040189;AB00917;AB02659;NSC-186903;N(.alpha.)-Benzyloxycarbonyl-L-glutamine;SY035724;SY041759;FT-0629944;FT-0629954;EN300-17223;F71962;2-benzyloxycarbonylamino-4-carbamoyl-butyric acid;SR-01000041091;SR-01000041091-1;Z56899133;5-amino-2-(benzyloxycarbonylamino)-5-oxopentanoic acid

Chemical Property of N~2~-[(benzyloxy)carbonyl]glutamine

Chemical Property:

• Appearance/Colour: white to off-white powder
• Vapor Pressure: 1.9E-15mmHg at 25°C
• Melting Point: 134-138 °C(lit.)
• Refractive Index: 1.6450 (estimate)
• Boiling Point: 604.2 °C at 760 mmHg
• PKA: 3.82±0.10(Predicted)
• Flash Point: 319.2 °C
• PSA: 118.72000
• Density: 1.316 g/cm³
• LogP: 1.72270
• Storage Temp.: -20°C
• Solubility.: DMSO, Ethanol, Methanol
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 280.10592162
• Heavy Atom Count: 20
• Complexity: 353

Purity/Quality:

99% ^*data from raw suppliers

Cbz-L-glutamine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NC(CCC(=O)N)C(=O)O
• Uses: N-Carbobenzyloxy-L-glutamine has use an anti-ulcer agent. Also an inhibitor for AHAS (Acetohydroxy Acid Synthase) an important enzyme which will affect how benign an environmental herbicid e is. Also used in the synthesis of neomycin B, an important HIV antiviral agent. N2-[(Phenylmethoxy)carbonyl]-L-glutamine has use an anti-ulcer agent. Also an inhibitor for AHAS (Acetohydroxy Acid Synthase) an important enzyme which will affect how benign an environmental herbicide is. Also used in the synthesis of neomycin B, an important HIV antiviral agent.

Technology Process of N~2~-[(benzyloxy)carbonyl]glutamine

There total 14 articles about N~2~-[(benzyloxy)carbonyl]glutamine 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: 98.0%

L-glutamine (56-85-9,26700-71-0) + N-Benzyloxycarbonyl-N-trifluoromethylsulfonyl-4-trifluoromethylanilide (250296-57-2) → Cbz-L-Gln (2650-64-8)

Guidance literature:

With water; triethylamine; In 1,4-dioxane; at 20 ℃; for 1h;

DOI:10.1039/a905561d

Reference yield: 98.0%

L-glutamine (56-85-9,26700-71-0) + benzyl chloroformate (501-53-1,94274-21-2) → Cbz-L-Gln (2650-64-8)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.tetlet.2015.04.037

Reference yield: 81.0%

L-glutamine (56-85-9,26700-71-0) + 3-benzyloxycarbonyl-2-oxazolone (75819-24-8) → Cbz-L-Gln (2650-64-8)

Guidance literature:

With triethylamine; In water; acetone; Ambient temperature;

upstream raw materials:

N-benzyloxycarbonyl-L-glutamic acid-5-hydrazide

(S)-2-(benzyloxycarbonylamino)-5-ethoxy-5-oxopentanoic acid

L-glutamine

benzyl chloroformate

Downstream raw materials:

benzyl 5-amino-2-(((benzyloxy)carbonyl)amino)-5-oxopentanoate

N²-benzyloxycarbonyl-L-glutamine methyl ester

(S)-methyl 5-amino-4-{[(benzyloxy)carbonyl]amino}-5-oxopentanoate

(S)-benzyl (2,6-dioxopiperidin-3-yl)carbamate

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF POMALIDOMIDE". Page/Page column 6-7. . Retrieved 2018/09/19.
• 2、 Liu, Shaoyu,Tang, Xiaolan,Nie, Dahong,Jiang, Shende,Tang, Ganghua. "Efficient synthesis of (2S)-tert-butyl 2-(2-bromopropanamido)-5-oxo-5-(tritylamino)pentanoate as a precursor of PET radiotracer [18F]FPGLN". supporting information. p. 1136 - 1141. Retrieved 2017/06/09.