63219-70-5

Usage

Uses

Used in Pharmaceutical Synthesis:
CBZ-D-PHENYLALANINAL is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to provide chiral selectivity, which is essential in the production of enantiomerically pure compounds. The presence of the carbobenzyloxy group aids in the formation of desired stereoisomers, enhancing the efficacy and safety of the resulting drugs.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, CBZ-D-PHENYLALANINAL is utilized as a chiral auxiliary to facilitate the synthesis of complex organic molecules with specific spatial arrangements. This is crucial for the development of new drugs with improved pharmacological properties and reduced side effects.
Used in Organic Synthesis:
CBZ-D-PHENYLALANINAL is employed as a chiral building block in organic synthesis, enabling the creation of a wide range of enantiomerically pure compounds. Its use in this context is vital for the production of specialty chemicals, agrochemicals, and other fine chemicals that require high levels of stereochemical control.
Used in Drug Development:
CBZ-D-PHENYLALANINAL is used as a precursor in the development of new drugs, where its chiral properties can be leveraged to create molecules with specific biological activities. CBZ-D-PHENYLALANINAL's role in drug development is to provide a foundation for the creation of innovative therapeutic agents that can address unmet medical needs.

Upstream product

• 59830-60-3 benzyl (1S)-(1-formyl-2-phenylethyl)carbamate 
• 6372-14-1 (2S)-2-(N-benzyloxycarbonyl)-amino-3-phenyl propanol 
• 59830-61-4 benzyl 1-benzyl-2,2-dimethoxyethylcarbamate 
• 1217341-14-4 C₁₈H₂₃NO₂ 
• 1084820-37-0 1,1-dimethoxy-3-phenylpropan-2-one oxime 
• 58917-85-4 N-(benzyloxycarbonyl)-D-phenylalaninol 
• 120452-49-5 N-methoxy-N-methyl-(R)-N²-Cbz-phenylalaninamide 
• 2448-45-5 Cbz-D-Phe 
• 37440-07-6 methyl (R)-2-(benzyloxycarbonylamino)-3-phenylpropanoate 
• 94234-87-4 C₁₇H₁₈Se 
• 31139-36-3 dibenzyl dicarbonate 
• 673-06-3 D-(R)-phenylalanine 
• 41518-17-6 C₂₂H₂₅NO₆ 
• 5267-64-1 (R)-2-amino-3-phenylpropanol 

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 
• 249296-51-3 (+/-)-3-[(Benzyloxycarbonyl)amino]-4-phenylbutan-2-ol 
• 130405-00-4 4-Benzyloxycarbonylamino-2,2-difluoro-3-hydroxy-5-phenyl-pentanoic acid,ethyl ester 
• 66413-45-4 3-(benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutanenitrile 
• 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 
• 207235-79-8 2-[5-benzyloxycarbonylamino-2-(4-fluorophenyl)-6-oxo-1,6-dihydro-1-pyrimidinyl]-N-[1-[(2-benzoxazolyl)hydroxymethyl]-2-phenylethyl]acetamide 
• 207234-95-5 2-[5-benzloxycarbonylamino-2-(4-fluorophenyl)-6-oxo-1,6-dihydro-1-pyrimidinyl]-N-[1-[(2-benzoxazolyl)carbonyl]-2-phenylethyl]acetamide 

Relevant academic research and scientific papers

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

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.

Resolution and absolute configuration of some a-aminoacetals: En route to enantiopure N-protected a-aminoaldehydes

The first successful resolution of rac-a-aminoacetals via diastereoisomeric salt formation with optically pure N-protected aminoacids is reported. The absolute configuration assignment of a-aminoacetal enantiomers is performed by an entirely non-racemizing chemical correlation method involving N-protection and a new efficient hydrolysis step followed by a reduction of the resulting N-protected a-aminoaldehyde intermediates. A racemization method of optically enriched a-aminoacetals is exemplified to allow valorisation of both enantiomers. Springer-Verlag 2011.

Carbonylation of functionalized diamine diols to cyclic ureas: Application to derivatives of DMP 450

Synthesis of the cyclic urea core structure of the HIV protease inhibitor DMP 450 has been achieved via W(CO)6/I2-catalyzed carbonylation of diamine intermediates. Carbonylations of related functionalized diamines to derivatives of the DMP 450 core structure were also examined. Selected diamine diol substrates could be converted to the cyclic urea core structure by catalytic carbonylation without protection of the diol functionality.

A novel and efficient synthesis of chiral C2-symmetric 1,4-diamines

A novel and efficient method for synthesis of (R,R)- and (S,S)-C2-symmetric 1,4-diamines was established. The key steps are a combination of Pinacol Coupling and Corey-Winter olefination.

PROCESS OF DEACETALISATION OF ALPHA AMINOACETALS

The invention relates to a process for the preparation of N-protected α-aminoaldehydes by deacetalization of the acetal functional group of corresponding N-protected α-aminoacetals using formic acid.

HYDROXYMORPHOLINONE DERIVATIVE AND MEDICINAL USE THEREOF

A compound represented by the following formula (I) wherein R1 and R2 are each a lower alkyl group optionally having substituents, which has a calpain inhibitory activity, or a salt thereof is provided.

Novel 6-Hydroxy-3-morpholinones as cornea permeable calpain inhibitors

A novel series of 6-hydroxy-3-morpholinones, in which the functional aldehyde and the hydroxy group of P2 site form a cyclic hemiacetal, was identified as calpain inhibitors. The placement of isobutyl group at the 2-position of the 3-morpholino

A novel concept in combinatorial chemistry in solution with the advantages of solid-phase synthesis: Formation of N-betaines by multicomponent domino reactions

Advantages of solid-phase and liquid-phase synthesis are combined in a new concept of combinatorial chemistry: a domino sequence comprising Knoevenagel and hetero-Diels-Alder reactions, with subsequent hydrogenation starting from protected aminoaldehydes, 1.3-dicarbonyl compounds, and enol ethers leads to N-heterocycles of high diversity with a betaine structure, which are isolated in highly pure form by precipitation with diethyl ether (see scheme), Cbz = benzylocycarbonyl, Bn = benzyl.

New synthetic technology for efficient construction of α-hydroxy-β-amino amides via the passerini reaction

The Passerini reaction of N-protected amino aldehydes, isonitriles, and TFA using pyridine-type bases proceeds under mild conditions and directly affords α-hydroxy-β-amino amide derivatives in moderate to high yields. These adducts are readily hydrolyzed to αhydroxy-β-amino carboxylic acids. Application of these key intermediates to concise syntheses of P1-α-ketoamide protease inhibitors is illustrated.