N-[(benzyloxy)carbonyl]leucylalanine

Base Information

• Chemical Name: N-[(benzyloxy)carbonyl]leucylalanine
• CAS No.: 2817-13-2
• Molecular Formula: C17H24N2O5
• Molecular Weight: 336.388
• Hs Code.: 2924299090
• NSC Number: 333758
• DSSTox Substance ID: DTXSID20950917
• Mol file: 2817-13-2.mol

Synonyms:N-[(benzyloxy)carbonyl]leucylalanine;212612-27-6;2-(2-{[(BENZYLOXY)CARBONYL]AMINO}-4-METHYLPENTANAMIDO)PROPANOIC ACID;2-[[4-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]propanoic acid;NSC333758;SCHEMBL9338295;DTXSID20950917;EINECS 220-571-1;BBL028368;STK366788;AKOS005443744;NSC 333758;NSC-333758;NCGC00332117-01;VS-08742;FT-0683988;EN300-717846;AB01326008-02;N-(N-((Phenylmethoxy)carbonyl)-L-leucyl)-L-alanine;N-(2-{[(Benzyloxy)(hydroxy)methylidene]amino}-1-hydroxy-4-methylpentylidene)alanine

Chemical Property of N-[(benzyloxy)carbonyl]leucylalanine

Chemical Property:

• Vapor Pressure: 2.26E-14mmHg at 25°C
• Melting Point: 150-155 °C
• Refractive Index: 1.529
• Boiling Point: 581.7 °C at 760 mmHg
• PKA: 3.51±0.10(Predicted)
• Flash Point: 305.6 °C
• PSA: 104.73000
• Density: 1.181 g/cm³
• LogP: 2.69860
• Storage Temp.: −20°C
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 336.16852187
• Heavy Atom Count: 24
• Complexity: 433

Purity/Quality:

98%min ^*data from raw suppliers

(S)-2-((S)-2-(((Benzyloxy)carbonyl)amino)-4-methylpentanamido)propanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(C(=O)NC(C)C(=O)O)NC(=O)OCC1=CC=CC=C1

Technology Process of N-[(benzyloxy)carbonyl]leucylalanine

There total 7 articles about N-[(benzyloxy)carbonyl]leucylalanine 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%

(S)-tert-butyl 2-((S)-2-(benzyloxycarbonylamino)-4-methylpentanamido)propanoate (53481-48-4) → ((S)-2-(benzyloxycarbonylamino)-4-methylpentanamido)propanoic acid (2817-13-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 2h;

DOI:10.1021/acs.jmedchem.9b01540

Reference yield: 85.0%

N-benzyloxycarbonyl-L-leucyl-L-alanine methyl ester (1803-59-4,22221-80-3,124169-21-7,4817-96-3) → ((S)-2-(benzyloxycarbonylamino)-4-methylpentanamido)propanoic acid (2817-13-2)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 1h;

DOI:10.1016/j.bmc.2004.07.016

Reference yield:

Z-Leu-OH (2018-66-8) → ((S)-2-(benzyloxycarbonylamino)-4-methylpentanamido)propanoic acid (2817-13-2)

Guidance literature:

With tetrahydrofuran; triethylamine; isobutyl chloroformate; anschliessend Behandeln mit L-Alanin und wss. NaOH;

DOI:10.1021/ja01638a049

upstream raw materials:

Z-Leu-OH

L-alanin

N-benzyloxycarbonyl-L-thioleucine S-phenyl ester

N-benzyloxycarbonyl-L-leucyl-L-alanine methyl ester

Downstream raw materials:

Leu-Ala

benzyl ((S)-1-(((S)-1-(methoxy(methyl)amino)-1-oxopropan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)carbamate

C₂₃H₃₃N₃O₆

C₂₃H₃₄N₂O₅

Refernces

• 1、 Osko, Jeremy D.,Porter, Nicholas J.,Narayana Reddy, Poli Adi,Xiao, You-Cai,Rokka, Johanna,Jung, Manfred,Hooker, Jacob M.,Salvino, Joseph M.,Christianson, David W.. "Exploring Structural Determinants of Inhibitor Affinity and Selectivity in Complexes with Histone Deacetylase 6". . p. 295 - 308. Retrieved 2020/02/20.
• 2、 Cerovsky, Vaclav,Martinek, Karel. "PEPTIDE SYNTHESIS CATALYZED BY NATIVE PROTEINASE K IN WATER-MISCIBLE ORGANIC SOLVENTS WITH LOW WATER CONTENT". . p. 2027 - 2041. Retrieved 2007/10/02.