63219-70-5

Basic information

• Product Name: CBZ-D-PHENYLALANINAL
• Synonyms: CBZ-D-PHENYLALANINAL;(R)-(+)-2-(Benzylcarbonylamino)-3-phenylpropanal;(R)-Benzyl (1-oxo-3-phenylpropan-2-yl)carbamate
• CAS NO: 63219-70-5
• Molecular Formula: C₁₇H₁₇NO₃
• Molecular Weight: 283.32178
• Mol File: 63219-70-5.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 482.266 °C at 760 mmHg
• Flash Point: 183.494 °C
• Appearance: /
• Density: 1.168
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: CBZ-D-PHENYLALANINAL(CAS DataBase Reference)
• NIST Chemistry Reference: CBZ-D-PHENYLALANINAL(63219-70-5)
• EPA Substance Registry System: CBZ-D-PHENYLALANINAL(63219-70-5)

Safety Data

• Hazardous Substances Data: 63219-70-5(Hazardous Substances Data)

Usage

Description

CBZ-D-PHENYLALANINAL, also known as N-CBZ-D-phenylalaninal, is a chemical compound that serves as a crucial building block in the synthesis of pharmaceuticals and organic compounds. It is a derivative of the amino acid phenylalanine, featuring a carbobenzyloxy (CBZ) group attached to the amino group, which provides it with unique properties as a chiral auxiliary in organic synthesis. This versatile chemical is integral to the development of various pharmaceuticals and plays a significant role in the field of medicinal chemistry.

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

• 42998-44-7 rac-N-benzyloxycarbonyl-phenylalanine ethyl ester 
• 150-30-1 Phenylalanine 
• 6372-14-1 (2S)-2-(N-benzyloxycarbonyl)-amino-3-phenyl propanol 
• 59830-60-3 benzyl (1S)-(1-formyl-2-phenylethyl)carbamate 
• 94234-87-4 C₁₇H₁₈Se 
• 31139-36-3 dibenzyl dicarbonate 
• 673-06-3 D-(R)-phenylalanine 
• 41518-17-6 C₂₂H₂₅NO₆ 
• 37440-07-6 methyl (R)-2-(benzyloxycarbonylamino)-3-phenylpropanoate 
• 5267-64-1 (R)-2-amino-3-phenylpropanol 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 2448-45-5 Cbz-D-Phe 
• 120452-49-5 N-methoxy-N-methyl-(R)-N²-Cbz-phenylalaninamide 
• 58917-85-4 N-(benzyloxycarbonyl)-D-phenylalaninol 

Downstream Products

• 130405-00-4 4-Benzyloxycarbonylamino-2,2-difluoro-3-hydroxy-5-phenyl-pentanoic acid,ethyl ester 
• 13326-10-8 benzyl methyl carbonate 
• 1026915-44-5 [1-{[1-benzyl-2-(5-diethylcarbamoyl-benzooxazol-2-yl)-2-oxo-ethylcarbamoyl]-methyl}-2-(4-fluoro-phenyl)-6-oxo-1,6-dihydro-pyrimidin-5-yl]-carbamic acid benzyl ester 
• 201677-80-7 2-[5-benzyloxycarbonylamino-6-oxo-2-(m-tolyl)-1,6-dihydro-1-pyrimidinyl]-N-[1-benzyl-3-[N-(3-tert-butyloxycarbonylphenyl)carbamoyl]-3,3-difluoro-2-oxopropyl]acetamide 
• 1027834-98-5 (1-{[1-benzyl-3,3-difluoro-2-hydroxy-3-(2-oxo-2-piperidin-1-yl-ethylcarbamoyl)-propylcarbamoyl]-methyl}-6-oxo-2-m-tolyl-1,6-dihydro-pyrimidin-5-yl)-carbamic acid benzyl ester 
• 228108-40-5 (1-{[1-benzyl-3,3-difluoro-2-oxo-3-(2-oxo-2-piperidin-1-yl-ethylcarbamoyl)-propylcarbamoyl]-methyl}-6-oxo-2-m-tolyl-1,6-dihydro-pyrimidin-5-yl)-carbamic acid benzyl ester 
• 228108-38-1 (1-{[3-(2-azepan-1-yl-2-oxo-ethylcarbamoyl)-1-benzyl-3,3-difluoro-2-oxo-propylcarbamoyl]-methyl}-6-oxo-2-m-tolyl-1,6-dihydro-pyrimidin-5-yl)-carbamic acid benzyl ester 
• 228108-70-1 (1-{[1-benzyl-3-(2-diethylcarbamoyl-ethylcarbamoyl)-3,3-difluoro-2-oxo-propylcarbamoyl]-methyl}-6-oxo-2-m-tolyl-1,6-dihydro-pyrimidin-5-yl)-carbamic acid benzyl ester 
• 207235-86-7 2-[5-benzyloxycarbonylamino-2-(4-fluorophenyl)-6-oxo-1,6-dihydro-1-pyrimidinyl]-N-[1-[[5-(ethylaminocarbonyl)benzoxazol-2-yl]hydroxymethyl]-2-phenylethyl]acetamide 
• 207235-05-0 2-[5-benzyloxycarbonylamino-2-(4-fluorophenyl)-6-oxo-1,6-dihydro-1-pyrimidinyl]-N-[1-[[5-(ethylaminocarbonyl)benzoxazol-2-yl]carbonyl]-2-phenylethyl]acetamide 
• 1026550-82-2 (1-{[1-benzyl-3-(diethylcarbamoylmethyl-carbamoyl)-3,3-difluoro-2-hydroxy-propylcarbamoyl]-methyl}-6-oxo-2-m-tolyl-1,6-dihydro-pyrimidin-5-yl)-carbamic acid benzyl ester 

Relevant articles and documents

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

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.

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.