16874-17-2

Basic information

• Product Name: (S)-3-PHENYLALANINE T-BUTYL ESTER
• Synonyms: (S)-3-PHENYLALANINE T-BUTYL ESTER;L-PHENYLALANINE-T-BUTYL ESTER;(S)-3-Phenylalaninetert-butylester;(2S)-2-Amino-3-phenylpropionic acid tert-butyl ester;L-Phenylalanine 1,1-dimethylethyl ester;L-Phenylalanine tert-butyl;L-Phe-OBut;Phenylalanine tert-butyl ester
• CAS NO: 16874-17-2
• Molecular Formula: C₁₃H₁₉NO₂
• Molecular Weight: 221.3
• Product Categories: Chiral Reagent
• Mol File: 16874-17-2.mol

Chemical Properties

• Boiling Point: 336.9 °C at 760 mmHg
• Flash Point: 157.6 °C
• Appearance: /
• Density: 1.042±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 7.09±0.33(Predicted)
• CAS DataBase Reference: (S)-3-PHENYLALANINE T-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-PHENYLALANINE T-BUTYL ESTER(16874-17-2)
• EPA Substance Registry System: (S)-3-PHENYLALANINE T-BUTYL ESTER(16874-17-2)

Safety Data

• Hazardous Substances Data: 16874-17-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(S)-3-Phenylalanine t-butyl ester is used as a building block in organic synthesis for the creation of various biologically active compounds. The t-butyl ester group provides stability and protection to the phenylalanine residue, facilitating easy manipulation in chemical reactions.
Used in Pharmaceutical Research:
In pharmaceutical research, (S)-3-Phenylalanine t-butyl ester serves as a chiral building block, playing a crucial role in the synthesis of pharmaceutical drugs. Its unique properties contribute to the development of new and effective medications.
Used in Peptide-based Drug and Material Preparation:
(S)-3-Phenylalanine t-butyl ester is utilized as a key intermediate in the preparation of peptide-based drugs and materials, where its structural and chemical characteristics are essential for the desired therapeutic effects.
Used in Drug Development:
Due to its unique structural and chemical properties, (S)-3-Phenylalanine t-butyl ester may have potential applications in the development of new drugs and materials, offering innovative solutions in the pharmaceutical and chemical industries.

Upstream product

• 16881-34-8 N-benzyloxycarbonyl-L-phenylalanine t-butyl ester 
• 63-91-2 L-phenylalanine 
• 115-11-7 isobutene 
• 78031-87-5 (S)-3-Phenyl-2-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonylamino)-propionic acid tert-butyl ester 
• 99744-54-4 N-<2-<(Dimethyl)(phenyl)phosphonio>isopropyloxycarbonyl>-L-phenylalanin-tert-butylester-chlorid 
• 99744-50-0 N-<2-<(Methyl)(diphenyl)phosphonio>isopropyloxycarbonyl>-L-phenylalanin-tert-butylester-chlorid 
• 99744-47-5 N-<2-(Triphenylphosphonio)isopropyloxycarbonyl>-L-phenylalanin-tert-butylester-chlorid 
• 188591-76-6 tert-butyl (2,2,2-trifluoroacetyl)-L-phenylalaninate 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 116400-16-9 N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine 1,1-dimethylethyl ester 
• 327026-67-5 Psoc-Phe-OtBu 
• 540-88-5 acetic acid tert-butyl ester 
• 882392-05-4 (S)-2-{[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-amino}-3-phenyl-propionic acid tert-butyl ester 
• 6456-74-2 Glycine tert-butyl ester 

Downstream Products

• 61900-41-2 (S)-tert-butyl-2-formamido-3-phenylpropanoate 
• 3799-57-3 N-(N-Trifluoracetyl-glycyl)-L-phenylalanin-tert.-butylester 
• 22839-72-1 N-Benzyloxycarbonyl-β-O-benzyl-Asp-Phe-tert.-butylester 
• 99744-34-0 N-(Trimethylsilyl)-L-Phe-t-butyl-ester 
• 73168-07-7 N-(Trimethylsiloxycarbonyl)-L-Phe-t-butyl-ester 
• 102344-22-9 p-Methoxy-carbobenzoxy-Glu(NH₂)-Phe-OBut 
• 104016-30-0 Z-α-Glu-Phe-O-t-Bu 
• 5105-84-0 N^α--N^γ-<3-tert-butoxycarbonylpropyl>-L-glutaminyl-L-phenylalanin-tert-butylester 
• 7669-70-7 Z-Glu(OBu-t)-Phe-OBu-t 
• 101399-00-2 (S)-tert-butyl 2-(2-(((benzyloxy)carbonyl)amino)acetamido)-3-phenylpropanoate 
• 116912-16-4 N-(Phenylacetyl)glycyl-L-phenylalanin-tert-butylester 
• 68277-06-5 (S)-N-acetylphenylalanine tert-butyl ester 
• 128992-39-2 N-Acetylphenylalanylphenylalanine tert-butyl ester 
• 128992-42-7 N-Acetylphenylalanylphenylalanine tert-butyl ester 

Relevant articles and documents

Conformational rearrangements by water-soluble peptoid foldamers

Peptoids are a family of N-substituted glycine oligomers that are capable of forming stable helical structures. We seek peptoid monomers that can establish a strong folding propensity in aqueous conditions. Here we utilize L-phenylalanine tert-butyl ester

Epoc group: Transformable protecting group with gold(iii)-catalyzed fluorene formation

This study presents the novel concept of a transformable protecting group, which changes its properties through structural transformation. Based on this concept, we developed a 2-(2-ethynylphenyl)-2-(5-methylfuran-2-yl)-ethoxycarbonyl (Epoc) group. The Epoc group was transformed into an Fmoc-like structure with gold(iii)-catalyzed fluorene formation and was removable under Fmoc-like mild basic conditions post-transformation even though it was originally stable under strongly basic conditions. As an application for organic synthesis, the Epoc group provides the novel orthogonality of gold(iii)-labile protecting groups in solid-phase peptide synthesis. In addition, the high turnover number of fluorene formation in aqueous media is suggestive of the applicability of the Epoc group to biological systems. This journal is

Overcoming the Deallylation Problem: Palladium(II)-Catalyzed Chemo-, Regio-, and Stereoselective Allylic Oxidation of Aryl Allyl Ether, Amine, and Amino Acids

We report herein a Pd(II)/bis-sulfoxide-catalyzed intramolecular allylic C-H acetoxylation of aryl allyl ether, amine, and amino acids with the retention of a labile allyl moiety. Mechanistically, the reaction proceeds through a distinct double-bond isomerization from the allylic to the vinylic position followed by intramolecular carboxypalladation and the β-hydride elimination pathway. For the first time, C-H oxidation of N-allyl-protected amino acids to furnish five-membered heterocycles through 1,3-syn-addition is established with excellent diastereoselectivity.

Synthesis of Dipeptides by Boronic Acid Catalysis

We have found that a boronic acid catalyzed amidation of an N -hydroxy amino acid methyl ester with amino acid tert -butyl esters gave N -hydroxy dipeptide derivatives in good yields without any racemization. The protecting groups on the nitrogen atom could be easily removed by heterogeneous hydrogenation conditions.

Heterocyclic derivatives with immunomodulatory effects

The invention relates to novel heterocyclic derivatives with immunomodulatory effects capable of inhibiting therapeutic agents in a programmed cell death (PD1) signal path. The compounds disclosed bythe invention are capable of enhancing antitumor activit

Probe compounds for fluorescence recognition of amino acid enantiomers and synthesis and applications thereof

The invention provides probe compounds for fluorescence recognition of amino acid enantiomers. Probe compounds (a, b, c) are prepared by following steps: dissolving dimethyl squarate into anhydrous methanol, dropwise adding methanol solutions of phenylalanine ethyl ester, phenylalanine benzyl ester, and phenylalanine tert-butyl ester, after addition, stirring the solution for 20 to 24 hours at a room temperature, filtering the solution, and finally washing the filter residues by ethyl acetate several times. When D-proline is added into ethanol-water solutions of chiral probe compounds (a, c),the fluorescence strength of the solutions is reduced; when L-proline is added into the solutions, the fluorescence strength of the solutions is enhanced obviously; and thus the probe compounds (a,c)have a good recognition effect on two enantiomers of proline. When L-valine is added into ethanol-water solutions of the probe compound (b), the fluorescence strength of the solution is obviously reduced; when D-valine is added into the solution, the fluorescence strength of the solution is not changed; and thus the probe compound (b) has a good recognition effect on two enantiomers of valine.

Enantioselective Synthesis of Quaternary Δ4- and Δ5-Dehydroprolines Based on a Two-Step Formal [3+2] Cycloaddition of α-Aryl and α-Alkyl Isocyano(thio)acetates with Vinyl Ketones

A divergent synthesis of optically active quaternary Δ4- and Δ5-dehydro prolines is developed based on the first catalytic enantioselective conjugate addition of α-substituted isocyano(thio)acetates to vinyl ketones that is general for both α-aryl and α-alkyl isocyano(thio)acetates. The new tetrasubstituted C?N stereocenter is formed without the need of any metal salt due to a bifunctional tertiary amine/squaramide catalyst, featuring a bulky polyaryl sidearm and an unusually short squaramide diamide H???H interatomic distance in the solid state.

4-Biphenylalanine- and 3-Phenyltyrosine-Derived Hydroxamic Acids as Inhibitors of the JumonjiC-Domain-Containing Histone Demethylase KDM4A

Overexpression of the histone lysine demethylase KDM4A, which regulates H3K9 and H3K36 methylation states, has been related to the pathology of several human cancers. We found that a previously reported hydroxamate-based histone deacetylase (HDAC) inhibitor (SW55) was also able to weakly inhibit this demethylase with an IC50value of 25.4 μm. Herein we report the synthesis and biochemical evaluations, with two orthogonal in vitro assays, of a series of derivatives of this lead structure. With extensive chemical modifications on the lead structure, also by exploiting the versatility of the radical arylation with aryldiazonium salts, we were able to increase the potency of the derivatives against KDM4A to the low-micromolar range and, more importantly, to obtain demethylase selectivity with respect to HDACs. Cell-permeable derivatives clearly showed a demethylase-inhibition-dependent antiproliferative effect against HL-60 human promyelocytic leukemia cells.

Recoverable Dendritic Phase-Transfer Catalysts that Contain (+)-Cinchonine-Derived Ammonium Salts

Four new phosphorus dendrimeric phase-transfer catalysts are prepared that contain 12 (+)-cinchoninium salts on the surface obtained by the quaternisation of the quinuclidinic N atom. The asymmetric alkylation of a glycinate Schiff base with benzyl bromide is used as a benchmark reaction, and the dendrimeric catalyst that contains an allyl group on the O-9 hydroxy group of the cinchonine units is the most active. The recovery and reuse of the catalyst are possible for five consecutive runs without loss of activity and with only a slight decrease in enantioselectivity. If other electrophiles are used, substituted benzyl bromides give better results than other activated alkyl bromides to afford the corresponding R amino acid derivatives. A comparison of these results with those reported previously for similar cinchoninium salts shows that dendrimers could be a better support than other polymers for this type of organocatalysis.

A mild, copper-catalysed amide deprotection strategy: Use of tert-butyl as a protecting group

Mild methods for the deprotection of organic substrates are of fundamental importance in synthetic chemistry. A new room temperature method using a catalytic amount of Cu(OTf)2is reported. This allows use of the tert-butyl group as an amide protecting group. The methodology is also extended to Boc-deprotection.