2018-66-8

Basic information

• Product Name: N-Cbz-L-Leucine
• Synonyms: BENZYLOXYCARBONYL-L-LEUCINE;CBZ-L-LEU-OH;CBZ-L-LEUCINE;CBZ-LEUCINE;CBZ-LEU-OH;N-ALPHA-BENZYLOXYCARBONYL-L-LEUCINE;N-CARBOBENZOXY-L-LEUCINE;N-BENZYLOXYCARBONYL-L-LEUCINE
• CAS NO: 2018-66-8
• Molecular Formula: C₁₄H₁₉NO₄
• Molecular Weight: 265.3
• EINECS: 217-960-3
• Product Categories: Amino Acid Derivatives;Leucine [Leu, L];Z-Amino Acids and Derivatives;Amino Acids;Amino Acids (N-Protected);Biochemistry;Cbz-Amino Acids;Z-Amino acid series
• Mol File: 2018-66-8.mol
• Article Data: 77

Chemical Properties

• Boiling Point: 408.52°C (rough estimate)
• Flash Point: 85 °F
• Appearance: /viscous liquid
• Density: 1 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.28E-08mmHg at 25°C
• Refractive Index: n20/D 1.512(lit.)
• Storage Temp.: 2-8°C
• PKA: 4.00±0.21(Predicted)
• Water Solubility: Not miscible or difficult to mix in water. Soluble in chloroform, DMSO and methanol.
• BRN: 1253861
• CAS DataBase Reference: N-Cbz-L-Leucine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Cbz-L-Leucine(2018-66-8)
• EPA Substance Registry System: N-Cbz-L-Leucine(2018-66-8)

Safety Data

• Hazard Codes: Xn
• Statements: 10-20/22-37/38-40-41-36/37/38-20/21/22-67-63-19
• Safety Statements: 16-26-36/37/39-45-36-36/37-60
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• RTECS: OH2921000
• Hazardous Substances Data: 2018-66-8(Hazardous Substances Data)

Usage

Description

N-Cbz-L-Leucine, also known as N-benzyloxycarbonyl-L-leucine, is a L-leucine derivative obtained by the substitution of a benzyloxycarbonyl group on the nitrogen atom. It is a yellow oil or weak solid and is used as a reactant in various chemical and pharmaceutical applications.

Uses

Used in Pharmaceutical Industry:
N-Cbz-L-Leucine is used as a reactant for the preparation of peptide-based potential antitumor agents. It plays a crucial role in the synthesis of peptides that have the potential to target and inhibit the growth of cancer cells.
Used in Chemical Synthesis:
N-Cbz-L-Leucine is used as a reactant for the preparation of cyclopropyl peptidomimetics. These peptidomimetics are synthetic compounds that mimic the structure and function of natural peptides, and they have potential applications in various fields, including drug discovery and development.
Used in Peptide Synthesis:
N-Cbz-L-Leucine is used as a building block in the synthesis of peptides. Its benzyloxycarbonyl protection group allows for the selective synthesis of complex peptide sequences, facilitating the development of novel therapeutic agents and other bioactive compounds.

InChI:InChI=1/C14H19NO4/c1-10(2)8-12(13(16)17)15-14(18)19-9-11-6-4-3-5-7-11/h3-7,10,12H,8-9H2,1-2H3,(H,15,18)(H,16,17)/t12-/m1/s1

Upstream product

• 61-90-5 L-leucine 
• 501-53-1 benzyl chloroformate 
• 40299-11-4 N-carbobenzoxy-L-leucine 4-nitrobenzyl ester 
• 920-36-5 (2-methylpropyl)lithium 
• 193091-62-2 (E)-(R)-O-(1-phenylbutyl)cinnamaldehyde oxime 
• 328-39-2 LEUCINE 
• 30293-88-0 N-carbonyl-L-leucine methyl ester 
• 91806-74-5 3,5-dimethyl-pyrazole-1-carboxylic acid benzyl ester 
• 127862-69-5 2-Benzyloxycarbonylamino-4-methyl-pentanoic acid 2,2,2-trifluoro-ethyl ester 
• 26054-60-4 ((S)-2-Oxo-oxetan-3-yl)-carbamic acid benzyl ester 
• 1068-55-9 isopropylmagnesium chloride 
• 204922-63-4 2-Benzyloxycarbonylamino-4-methyl-4-nitro-pentanoic acid methyl ester 
• 100-51-6 benzyl alcohol 
• 687-51-4 H-L-Leu-NH₂ 

Downstream Products

• 1738-87-0 Z-Leu-ONp 
• 7801-70-9 Z-Leu-Val 
• 18791-60-1 S-benzyl-N-(N-benzyloxycarbonyl-L-leucyl)-L-cysteine 
• 103267-29-4 N-(N-benzyloxycarbonyl-L-leucyl)-L-tyrosine benzyl ester 
• 103327-58-8 N-[S-benzyl-N-(N-benzyloxycarbonyl-L-leucyl)-L-cysteinyl]-glycine benzyl ester 
• 103820-93-5 ethyl N-benzyloxycarbonyl-L-leucyl-L-tyrosinate 
• 104295-15-0 N-benzyloxycarbonyl-L-leucine-(4-methoxy-[2]naphthylamide) 
• 3005-89-8 ethyl N-benzyloxycarbonyl-L-leucyl-L-phenylalaninate 
• 122411-96-5 S-benzyl-N-(N-benzyloxycarbonyl-L-leucyl)-L-cysteine ethyl ester 
• 3005-89-8 N-(N-benzyloxycarbonyl-L-leucyl)-Ξ-phenylalanine ethyl ester 
• 111411-33-7 N-benzyloxycarbonyl-L-thioleucine S-(4-nitro-phenyl ester) 
• 5084-98-0 methyl N-benzyloxycarbonyl-L-leucylglicynate 
• 3504-37-8 Cbz-L-Leu-L-Leu-OMe 
• 2276-20-2 N-(N-benzyloxycarbonyl-L-leucyl)-glycine amide 

Relevant articles and documents

Design and synthesis of novel symmetric fluorene-2,7-diamine derivatives as potent hepatitis C virus inhibitors

Hepatitis C virus (HCV) is an international challenge. Since the discovery of NS5A direct-acting antivirals, researchers turned their attention to pursue novel NS5A inhibitors with optimized design and structure. Herein we explore highly potent hepatitis C virus (HCV) NS5A inhibitors; the novel analogs share a common symmetrical prolinamide 2,7-diaminofluorene scaffold. Modification of the 2,7-diaminofluorene backbone included the use of (S)-prolinamide or its isostere (S,R)-piperidine-3-caboxamide, both bearing different amino acid residues with terminal carbamate groups. Compound 26 exhibited potent inhibitory activity against HCV genotype (GT) 1b (effective concentration (EC50) = 36 pM and a selectivity index of >2.78 × 106). Compound 26 showed high selectivity on GT 1b versus GT 4a. Interestingly, it showed a significant antiviral effect against GT 3a (EC50 = 1.2 nM). The structure-activity relationship (SAR) analysis revealed that picomolar inhibitory activity was attained with the use of S-prolinamide capped with R- isoleucine or R-phenylglycine residues bearing a terminal alkyl carbamate group.

A Next-Generation Air-Stable Palladium(I) Dimer Enables Olefin Migration and Selective C?C Coupling in Air

We report a new air-stable PdI dimer, [Pd(μ-I)(PCy2tBu)]2, which triggers E-selective olefin migration to enamides and styrene derivatives in the presence of multiple functional groups and with complete tolerance of air. The same dimer also triggers extremely rapid C?C coupling (alkylation and arylation) at room temperature in a modular and triply selective fashion of aromatic C?Br, C?OTf/OFs, and C?Cl bonds in poly(pseudo)halogenated arenes, displaying superior activity over previous PdI dimer generations for substrates that bear substituents ortho to C?OTf.

PEPTIDOMIMETICS FOR THE TREATMENT OF CORONAVIRUS AND PICORNAVIRUS INFECTIONS

Compounds, compositions and methods for preventing, treating or curing a coronavirus, picornavirus, and/or Hepeviridae virus infection in human subjects or other animal hosts. Specific viruses that can be treated include enteroviruses. In one embodiment, the compounds can be used to treat an infection with a severe acute respiratory syndrome virus, such as human coronavirus 229E, SARS, MERS, SARS-CoV-1 (OC43), and SARS-CoV- 2. In another embodiment, the methods are used to treat a patient co-infected with two or more of these viruses, or a combination of one or more of these viruses and norovirus.