59830-60-3

Usage

Uses

Used in Pharmaceutical Industry:
CBZ-L-PHENYLALANINAL is used as a starting material for the synthesis of various pharmaceuticals and fine chemicals. Its versatility in reacting with different functional groups allows for the creation of a wide range of chemical compounds.
CBZ-L-PHENYLALANINAL is used as a chemical building block for the development of new drugs and chemical compounds due to its selective reactivity with various functional groups.
Used in Chemical Synthesis:
CBZ-L-PHENYLALANINAL is used as a versatile reagent in chemical synthesis processes, enabling the formation of a diverse array of chemical compounds.
CBZ-L-PHENYLALANINAL is used as a selective reactant with carboxylic acids, amines, and other functional groups, contributing to the synthesis of complex molecules in the chemical industry.
Used in Enzyme and Receptor Inhibition Studies:
CBZ-L-PHENYLALANINAL is used as a potential inhibitor of certain enzymes and receptors in the human body, which has been studied for its pharmacological properties.
CBZ-L-PHENYLALANINAL is used in research and development for its potential to modulate biological processes through enzyme and receptor inhibition, offering new avenues for therapeutic intervention.

Upstream product

• 6372-14-1 (2S)-2-(N-benzyloxycarbonyl)-amino-3-phenyl propanol 
• 3588-57-6 Z-DL-Phe-OH 
• 3182-93-2 ethyl 2-amino-3-phenylpropanoate hydrochloride 
• 6372-14-1 N-((benzyloxy)carbonyl)-L-phenylalaninol 
• 1217341-14-4 C₁₈H₂₃NO₂ 
• 1084820-37-0 1,1-dimethoxy-3-phenylpropan-2-one oxime 
• 62750-39-4 1-<(Benzyl-carbobenzoxyamino)-acetyl>-imidazol 
• 1161-13-3 N-Cbz-L-Phe 
• 35909-92-3 N-carbobenzoxy-L-phenylalanine methyl ester 
• 28709-70-8 N-benzyloxycarbonyl-L-phenylalanine ethyl ester 
• 114744-85-3 [(S)-1-(methoxy-methyl-carbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester 
• 25613-60-9 Nα-carbobenzyloxy-L-phenylalanine N-carboxanhydride 
• 133010-22-7 benzyl (S)-(1-fluoro-1-oxo-3-phenylpropan-2-yl)carbamate 
• 60718-38-9 (S)-2-benzyloxycarbonylamino-3-phenylthiopropanoic acid S-ethyl ester 

Downstream Products

• 68437-25-2 7c-benzyl-5,6t-dimethyl-1,9-dioxo-(3ar,6ac,9acC¹)-3a,6,6a,7-tetrahydro-3H-furo[3,4-d]isoindole-8-carboxylic acid benzyl ester 
• 86827-22-7 rac-dimethyl 2-<2'-(benzyloxycarbonylamino)-3'-phenylpropylidene> malonate 
• 130405-00-4 4-Benzyloxycarbonylamino-2,2-difluoro-3-hydroxy-5-phenyl-pentanoic acid,ethyl ester 
• 902151-18-2 [1-benzyl-2-hydroxy-5-(tetrahydro-pyran-2-yloxy)-pent-3-ynyl]-carbamic acid benzyl ester 
• 207235-45-8 2-[5-benzyloxycarbonylamino-6-oxo-2-(4-pyridyl)-1,6-dihydro-1-pyrimidinyl]-N-[1-[[5-(methoxycarbonyl)benzoxazol-2-yl]carbonyl]-2-phenylethyl]acetamide 
• 1060718-86-6 2-{2-[2-(5-benzyloxycarbonylamino-6-oxo-2-pyridin-4-yl-6H-pyrimidin-1-yl)-acetylamino]-1-hydroxy-3-phenyl-propyl}-benzooxazole-5-carboxylic acid methyl ester 
• 207235-88-9 2-[5-benzyloxycarbonylamino-2-(4-fluorophenyl)-6-oxo-1,6-dihydro-1-pyrimidinyl]-N-[1-[(5-methoxybenzoxazol-2-yl)hydroxymethyl]-2-phenylethyl]acetamide 
• 207235-12-9 [1-{[1-benzyl-2-(5-methoxy-benzooxazol-2-yl)-2-oxo-ethylcarbamoyl]-methyl}-2-(4-fluoro-phenyl)-6-oxo-1,6-dihydro-pyrimidin-5-yl]-carbamic acid benzyl ester 
• 1026347-40-9 2-{2-[2-(5-benzyloxycarbonylamino-6-oxo-2-pyridin-3-yl-6H-pyrimidin-1-yl)-acetylamino]-3-phenyl-propionyl}-benzooxazole-5-carboxylic acid methyl ester 
• 1026149-29-0 2-{2-[2-(5-benzyloxycarbonylamino-6-oxo-2-phenyl-6H-pyrimidin-1-yl)-acetylamino]-3-phenyl-propionyl}-benzooxazole-5-carboxylic acid methyl ester 
• 1059698-66-6 2-{2-[2-(5-benzyloxycarbonylamino-6-oxo-2-pyridin-3-yl-6H-pyrimidin-1-yl)-acetylamino]-1-hydroxy-3-phenyl-propyl}-benzooxazole-5-carboxylic acid methyl ester 
• 105507-42-4 (+/-)-3-[(Benzyloxycarbonyl)amino]-4-phenylbutan-2-one 

Relevant academic research and scientific papers

The Chemical Development of LB71350

An efficient synthesis of the HIV-1 protease inhibitor LB71350 (1) is described. High diastereoselective epoxidation of the cis-allylic carbamate fragment of (5S)-[N-(benzyloxycarbonyl)-amino]-N-[2-methyl-(1R)-[(phenyl) carbonyl]-propyl]-6-phenylhex-(Z)-e

Probing α-Amino Aldehydes as Weakly Acidic Pronucleophiles: Direct Access to Quaternary α-Amino Aldehydes by an Enantioselective Michael Addition Catalyzed by Br?nsted Bases

The high tendency of α-amino aldehydes to undergo 1,2-additions and their relatively low stability under basic conditions have largely prevented their use as pronucleophiles in the realm of asymmetric catalysis, particularly for the production of quaternary α-amino aldehydes. Herein, it is demonstrated that the chemistry of α-amino aldehydes may be expanded beyond these limits by documenting the first direct α-alkylation of α-branched α-amino aldehydes with nitroolefins. The reaction produces densely functionalized products bearing up to two, quaternary and tertiary, vicinal stereocenters with high diastereo- and enantioselectivity. DFT modeling leads to the proposal that intramolecular hydrogen bonding between the NH group and the carbonyl oxygen atom in the starting α-amino aldehyde is key for reaction stereocontrol.

Discovery of Peptidomimetic Antibody-Drug Conjugate Linkers with Enhanced Protease Specificity

Antibody-drug conjugates (ADCs) have become an important therapeutic modality for oncology, with three approved by the FDA and over 60 others in clinical trials. Despite the progress, improvements in ADC therapeutic index are desired. Peptide-based ADC linkers that are cleaved by lysosomal proteases have shown sufficient stability in serum and effective payload-release in targeted cells. If the linker can be preferentially hydrolyzed by tumor-specific proteases, safety margin may improve. However, the use of peptide-based linkers limits our ability to modulate protease specificity. Here we report the structure-guided discovery of novel, nonpeptidic ADC linkers. We show that a cyclobutane-1,1-dicarboxamide-containing linker is hydrolyzed predominantly by cathepsin B while the valine-citrulline dipeptide linker is not. ADCs bearing the nonpeptidic linker are as efficacious and stable in vivo as those with the dipeptide linker. Our results strongly support the application of the peptidomimetic linker and present new opportunities for improving the selectivity of ADCs.

Regioselective Fluorination of α-Hydroxy-β-aminophosphonates by Using PyFluor

We report a simple protocol for the synthesis of α-fluoro-β-aminophosphonates by the regioselective fluorination of α-hydroxy-β-aminophosphonates under mild conditions. The fluorination reactions were mediated by the PyFluor reagent and occurred with the retention of configuration. The main products of this reaction were a series of α-fluoro-β-aminophosphonates, which can be used as precursors in the preparation of medicinally important compounds (e.g., dipeptide analogues).

Burgess Reagent Facilitated Alcohol Oxidations in DMSO

The Burgess reagent ([methoxycarbonylsulfamoyl]triethylammonium hydroxide) has historically found utility as a dehydrating agent. Herein we show that, in the presence of dimethyl sulfoxide, the Burgess reagent efficiently and rapidly facilitates the oxidation of a broad range of primary and secondary alcohols to their corresponding aldehydes and ketones in excellent yields and under mild conditions, and can be combined with other transformations (e.g., Wittig olefinations). A mechanism similar to those described for the Pfitzner-Moffatt and Swern oxidations is proposed.

Amino Aldehydes Revisited

The enzymatic oxidation of amino alcohols was studied to address the long-standing problem of product stability. Amino aldehydes, highly sought and unstable compounds, can be generated under mild conditions if they are immediately protected. Utilizing a r

Discovery of Novel and Highly Selective Inhibitors of Calpain for the Treatment of Alzheimer's Disease: 2-(3-Phenyl-1H-pyrazol-1-yl)-nicotinamides

Calpain overactivation has been implicated in a variety of pathological disorders including ischemia/reperfusion injury, cataract formation, and neurodegenerative diseases such as Alzheimer's disease (AD). Herein we describe our efforts leading to the ide

Aminooxylation Horner-Wadsworth-Emmons Sequence for the Synthesis of Enantioenriched γ-Functionalized Vinyl Sulfones

An operationally simple protocol for the synthesis of γ-hydroxy vinyl sulfones has been developed using a proline-based aldehyde aminooxylation, followed by a vinyl sulfone forming Horner-Wadsworth-Emmons olefination. The adducts, formed in high enantiopurity, were subsequently converted to γ-azido vinyl sulfones, and azide-alkyne click chemistry enabled the synthesis of vinyl sulfone-based triazoles as potential nonpeptidic cysteine protease inhibitors. (Chemical Equation Presented).

Immunomodulators

The present disclosure provides novel macrocyclic peptides which inhibit the PD-1/PD-L1 and PD-L1/CD80 protein/protein interaction, and thus are useful for the amelioration of various diseases, including cancer and infectious diseases.

A rapid and efficient one-pot method for the reduction of N-protected α-amino acids to chiral α-amino aldehydes using CDI/DIBAL-H

N-Protected amino acids can be easily converted into chiral α-amino aldehydes in a one-pot reaction by activation with CDI followed by reduction with DIBAL-H. This method delivers Boc-, Cbz- and Fmoc-protected amino aldehydes from proteinogenic amino acids in very good isolated yields and complete stereointegrity.