2899-07-2

Basic information

• Product Name: Cbz-N-methyl-L-phenylalanine
• Synonyms: N-ALPHA-CBZ-N-ALPHA-METHYL-L-PHENYLALANINE;N-ALPHA-CARBOBENZOXY-N-ALPHA-METHYL-L-PHENYLALANINE;N-CBZ-N-METHYL-L-PHENYLALANINE;Z-N-METHYL-L-PHENYLALANINE;Z-MEPHE-OH;Z-N-ME-PHENYLALANINE;Z-N-ME-PHE-OH;CBZ-N-ME-PHE-OH
• CAS NO: 2899-07-2
• Molecular Formula: C₁₈H₁₉NO₄
• Molecular Weight: 313.35
• Product Categories: N-Methyl Amino Acids;Amino Acid Derivatives
• Mol File: 2899-07-2.mol
• Article Data: 16

Chemical Properties

• Melting Point: 67.0 to 71.0 °C
• Boiling Point: 484.96 °C at 760 mmHg
• Flash Point: 247.095 °C
• Appearance: /
• Density: 1.23 g/cm³
• Vapor Pressure: 3.23E-10mmHg at 25°C
• Refractive Index: 1.588
• Storage Temp.: Store at RT.
• CAS DataBase Reference: Cbz-N-methyl-L-phenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: Cbz-N-methyl-L-phenylalanine(2899-07-2)
• EPA Substance Registry System: Cbz-N-methyl-L-phenylalanine(2899-07-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 2899-07-2(Hazardous Substances Data)

Usage

General Description

Cbz-N-methyl-L-phenylalanine is a chemical compound known for its function in the field of biochemistry, particularly in peptide synthesis. The "Cbz" refers to 'carbobenzyloxy' which is a protecting group used in organic synthesis, the N-methyl indicates an added methyl group, and L-phenylalanine refers to the amino acid phenylalanine in the L-isomer form. The compound is often used in research and laboratory settings due to its influence on biochemical reactions, more specifically in preventing certain reactions from happening prematurely. Therefore, Cbz-N-methyl-L-phenylalanine is essential for the control and effectiveness of scientific experimentations involving peptide synthesis.

InChI:InChI=1/C18H19NO4/c1-19(18(22)23-13-15-10-6-3-7-11-15)16(17(20)21)12-14-8-4-2-5-9-14/h2-11,16H,12-13H2,1H3,(H,20,21)/t16-/m0/s1

Upstream product

• 2566-30-5 N-Methyl-L-phenylalanine 
• 501-53-1 benzyl chloroformate 
• 55740-07-3 (4S)-4-benzyl-5-oxo-1,3-oxazolidine-3-carboxylic acid benzyl ester 
• 1161-13-3 N-Cbz-L-Phe 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 
• 24164-73-6 methyl (S)-2-(benzyloxycarbonyl-methyl-amino)-3-phenylpropionate 
• 35909-92-3 N-carbobenzoxy-L-phenylalanine methyl ester 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 15058-52-3 benzyl hydroxy(methyl)carbamate 
• 104-53-0 3-phenyl-propionaldehyde 
• 1448581-73-4 benzyl 2,4-dinitrophenylsulfonyloxy(methyl)carbamate 
• 50-00-0 formaldehyd 

Downstream Products

• 17191-53-6 Cbz-(NMe)Phe-NH₂ 
• 24164-73-6 methyl (S)-2-(benzyloxycarbonyl-methyl-amino)-3-phenylpropionate 
• 114525-93-8 Cbz-(Me)Phe-Ot-Bu 
• 192064-88-3 (S)-2-[(S)-2-(Benzyloxycarbonyl-methyl-amino)-3-phenyl-propionylamino]-3-(1H-imidazol-4-yl)-propionic acid methyl ester 
• 201408-95-9 (S)-2-[(S)-2-(Benzyloxycarbonyl-methyl-amino)-3-phenyl-propionylamino]-3-(3-trityl-3H-imidazol-4-yl)-propionic acid methyl ester 
• 202134-42-7 (2S)-benzyl 1-hydroxy-3-phenylpropan-2-yl(methyl)carbamate 
• 220657-13-6 (2S,3R)-3-[(S)-2-(Benzyloxycarbonyl-methyl-amino)-3-phenyl-propionyloxy]-2-tert-butoxycarbonylamino-butyric acid 2-trimethylsilanyl-ethoxymethyl ester 
• 180597-97-1 4-benzyl-3-methoxazolidine-2,5-dione 
• 603121-69-3 benzyl (1S)-1-benzyl-2-{[2-(3,4-dimethoxyphenyl)ethyl]amino}-2-oxoethyl(methyl)carbamate 
• 2566-30-5 N-Methyl-L-phenylalanine 
• 922705-73-5 phenylmethyl [(1S)-3-diazo-2-oxo-1-(phenylmethyl)propyl]methylcarbamate 
• 927438-78-6 2-[2-(benzyloxycarbonyl-methyl-amino)-3-phenyl-propionylamino]-3-methyl-butyric acid tert-butyl ester 
• 766513-71-7 (2S,3R)-3-((S)-2-{[(S)-1-((S)-2-Amino-4-methyl-pentanoyl)-pyrrolidine-2-carbonyl]-methyl-amino}-3-phenyl-propionyloxy)-2-tert-butoxycarbonylamino-butyric acid 2-trimethylsilanyl-ethoxymethyl ester 
• 766513-73-9 (20-benzyl-5-isobutyl-8,13-diisopropyl-17,21-dimethyl-4,7,10,15,19,22-hexaoxo-12-triisopropylsilanyloxy-eicosahydro-9,18-dioxa-3a,6,14,21-tetraaza-cyclopentacycloheneicosen-16-yl)-carbamic acid tert-butyl ester 

Relevant articles and documents

Synthesis of N-Benzyloxycarbonyl-N-methylaminoacids from Oxazolidine-5-one Derivatives

Hydrogenolysis of 3-benzyloxycarbonyloxazolidine-5-one and 3-benzyloxycarbonyl-4-benzyloxazolidine-5-one by Et3SiH in the presence of F3CCO2H is demonstrated to be a convenient method for preparing substituted N-methylaminoacids.In contrast with catalytic

Enantioselective direct α-amination of aldehydes via a photoredox mechanism: A strategy for asymmetric amine fragment coupling

The direct, asymmetric α-amination of aldehydes has been accomplished via a combination of photoredox and organocatalysis. Photon-generated N-centered radicals undergo enantioselective α-addition to catalytically formed chiral enamines to directly produce stable α-amino aldehyde adducts bearing synthetically useful amine substitution patterns. Incorporation of a photolabile group on the amine precursor obviates the need to employ a photoredox catalyst in this transformation. Importantly, this photoinduced transformation allows direct and enantioselective access to α-amino aldehyde products that do not require postreaction manipulation.

Total synthesis and biological evaluation of tamandarin B analogues

(Chemical Equation Presented) Tamandarins A and B are a class of marine natural cyclodepsipeptides with structures and biological activities closely related to those of the didemnins. The easier synthetic access to tamandarins accelerates the preparation of new macrocyclic derivatives of this family of antitumor, antiviral, and immunosuppressive compounds. The optimization of the previously reported synthetic route to tamandarins by changing the macrolactamization site from Nst1 and Thr6 to Pro 4 and N,O-Me2Tyr5 residues led to a significant improvement in the reaction yield. Using this new synthetic approach, four new macrocyclic analogues of tamandarin B were prepared and evaluated for anticancer activity. These results provide further insight into the structure-activity relationship of the tamandarins and didemnins.