N-Carbobenzyloxy-L-valine

Base Information

• Chemical Name: N-Carbobenzyloxy-L-valine
• CAS No.: 1149-26-4
• Molecular Formula: C13H17NO4
• Molecular Weight: 251.282
• Hs Code.: 2924.29 DERIVATION
• European Community (EC) Number: 214-562-1
• UNII: B7E8KBA5JX
• Nikkaji Number: J80.203D
• Wikidata: Q63392261
• Mol file: 1149-26-4.mol

Synonyms:1149-26-4;N-CBZ-L-VALINE;Z-Val-OH;N-Carbobenzyloxy-L-valine;CBZ-L-valine;Z-L-Valine;N-Carbobenzoxy-L-valine;Z-L-VAL-OH;Carbobenzoxy-L-valine;z-valine;Carbobenzyloxy-L-valine;Benzyloxycarbonyl-L-valine;N-Benzyloxycarbonyl-L-valine;Cbz-VAL-OH;(2S)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanoic acid;(2S)-3-methyl-2-(phenylmethoxycarbonylamino)butanoic acid;L-Valine, N-[(phenylmethoxy)carbonyl]-;((Benzyloxy)carbonyl)-L-valine;N-(Benzyloxycarbonyl)-L-valine;(S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanoic acid;(2S)-2-{[(BENZYLOXY)CARBONYL]AMINO-3-METHYLBUTANOIC ACID;MFCD00008922;N-benzyloxycarbonylvaline;B7E8KBA5JX;(S)-N-(benzyloxycarbonyl)valine;L-VALINE, N-((PHENYLMETHOXY)CARBONYL)-;EINECS 214-562-1;Cbz-Valine;N-Cbz-valine;Cbz-Val;Cbz-(L)-valine;(s)-n-cbz-valine;CBZ-(S)-valine;N-CBZ-L -valine;N-Cbz-Val-OH;2-(Benzyloxycarbonylamino)-3-methylbutanoic acid;carbobenzoxy-(S)-valine;Z-(L)-Val-OH;SCHEMBL220569;Carbobenzyloxy-L-valine, 99%;N-(benzyioxycarbonyl)-L-valine;L-VALINE, N-CBZ PROTECTED;N-[(benzyloxy)carbonyl]-L-valine;STR06192;AKOS010371619;AKOS015924215;AC-7044;CCG-256518;CS-W009469;AC-24056;AS-12745;AM20060476;EN300-121294;M03071;P16425;(S)-2-benzyloxycarbonylamino-3-methyl-butyric acid;J-300300;J-506251;N-alpha-BenZyloxycarbonyl-L-valine (CbZ-L-Val-OH);Q-101854;Q63392261;2-(S)-[(benzyloxycarbonyl)amino]-3-methylbutyric acid;(S)-2-(BENZYLOXYCARBONYLAMINO)-3-METHYLBUTANOIC ACID;(2S)-2-((BENZYLOXYCARBONYL)AMINO)-3-METHYLBUTANOIC ACID

Chemical Property of N-Carbobenzyloxy-L-valine

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 2.99E-08mmHg at 25°C
• Melting Point: 62-64 °C(lit.)
• Refractive Index: -4.3 ° (C=2, AcOH)
• Boiling Point: 432.6 °C at 760 mmHg
• PKA: 4.00±0.10(Predicted)
• Flash Point: 215.4 °C
• PSA: 75.63000
• Density: 1.182 g/cm³
• LogP: 2.41290
• Storage Temp.: 2-8°C
• Solubility.: Acetic Acid, DMSO (Slightly), Ethanol (Slightly)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 251.11575802
• Heavy Atom Count: 18
• Complexity: 285

Purity/Quality:

99% ^*data from raw suppliers

Z-L-valine 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 38-43-36/37/38-20/21/22
• Safety Statements: 36/37-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)C(C(=O)O)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CC(C)[C@@H](C(=O)O)NC(=O)OCC1=CC=CC=C1
• Uses: Imatinib intermediate Valaciclovir intermediate N-Cbz-L-valine is an N-Cbz-protected form of L-Valine (V094205). L-Valine is an essential amino acid that is used as an ingredient in cosmetic formulations, pharmaceuticals, and animal feed products. L-valine is also important for growth and ammonia detoxification in humans.

Technology Process of N-Carbobenzyloxy-L-valine

There total 50 articles about N-Carbobenzyloxy-L-valine 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: 92.0%

(S)-2-Benzyloxycarbonylamino-3-methyl-butyric acid 3-methyl-but-2-enyl ester → (S)-N-(benzyloxycarbonyl)valine (1149-26-4)

Guidance literature:

With cerium(III) chloride; sodium iodide; In acetonitrile; for 2h; Heating;

DOI:10.1055/s-2002-19320

Reference yield: 91.0%

L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) + 1-Benzyloxycarbonylbenzimidazoline-2-thione (91285-93-7) → (S)-N-(benzyloxycarbonyl)valine (1149-26-4)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; for 12h; Ambient temperature;

DOI:10.1055/s-1985-31329

Reference yield: 90.0%

L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) + N-(benzyloxycarbonyl)benzothiazolin-2-thione (91285-92-6) → (S)-N-(benzyloxycarbonyl)valine (1149-26-4)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; for 12h; Ambient temperature;

DOI:10.1055/s-1985-31329

upstream raw materials:

D,L-valine

benzyl chloroformate

3,5-dimethyl-pyrazole-1-carboxylic acid benzyl ester

tert-butyl 2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate

Downstream raw materials:

N-benzyloxycarbonyl-valine 4-nitro-phenyl ester

N-(N-benzyloxycarbonyl-valyl)-alanine ethyl ester

Z-Val-Glu(OMe)2

Z-Val-ONp

Refernces

• 1、 Abadi, Ashraf H.,Abdallah, Mennatallah,Abdel-Halim, Mohammad,Bartenschlager, Ralf,Frakolaki, Efseveia,Hamed, Mostafa M.,Hirsch, Anna K. H.,Katsamakas, Sotirios,Vassilaki, Niki,Zoidis, Grigoris. "Redesigning of the cap conformation and symmetry of the diphenylethyne core to yield highly potent pan-genotypic NS5A inhibitors with high potency and high resistance barrier". . . Retrieved 2021/12/27.
• 2、 Hattori, Tetsutaro,Kitamoto, Yuichi,Maeda, Tetsuya,Miyoshi, Ikuko,Morohashi, Naoya. "Enantioselective inclusion of pyrene-1-sulfonate salts of α-amino acids with crystals of α-cyclodextrin". supporting information. . Retrieved 2020/04/01.