21691-50-9

Usage

Uses

Used in Organic Synthesis:
Tert-butyl L-alaninate is used as a reagent in organic synthesis for the preparation of various chemical compounds. Its versatility in chemical reactions makes it a valuable component in the synthesis of complex molecules.
Used in Pharmaceutical Industry:
Tert-butyl L-alaninate is used as an intermediate in the preparation of pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its role in the synthesis of biologically active molecules allows for the creation of potential treatments for various medical conditions.
Used in Peptide Synthesis:
In the field of peptide synthesis, tert-butyl L-alaninate is used as a building block for the creation of alanine residues. This is crucial for the development of peptides and proteins with specific functions and properties, which can be applied in research, medicine, and biotechnology.

InChI:InChI=1/C7H15NO2/c1-5(8)6(9)10-7(2,3)4/h5H,8H2,1-4H3/t5-/m0/s1

Upstream product

• 56-41-7 L-alanin 
• 115-11-7 isobutene 
• 1245735-66-3 Fms-Ala-OtBu 
• 226900-13-6 tert-butyl N-(diphenylmethylene)alaninate 
• 76849-54-2 t-butyl pyruvate 
• 81477-94-3 N-(diphenylmethylene)glycine tert-butyl ester 
• 74-88-4 methyl iodide 
• 540-88-5 acetic acid tert-butyl ester 
• 13404-22-3 tert-butyl L-alaninate hydrochloride 
• 875433-31-1 (2S)-N-[9-(4-bromophenyl)-9-fluorenyl]alanine tert-butyl ester 
• 875433-32-2 (2S)-N-(9-(4-morpholinophenyl)-9-fluorenyl)alanine tert-butyl ester 
• 50300-96-4 (S)-2-(benzyloxycarbonylamino)propionic acid tert-butyl ester 
• 1142-20-7 N-Cbz-Ala 

Downstream Products

• 58177-77-8 N-[(1,1-dimethylethoxy)carbonyl]-L-alanine 1,1-dimethylethyl ester 
• 62632-23-9 (S)-tert-butyl 2-(2-(((benzyloxy)carbonyl)amino)acetamido)propanoate 
• 59903-66-1 (S)-2-[1-Methyl-2-phenyl-eth-(Z)-ylideneamino]-propionic acid tert-butyl ester 
• 161007-06-3 Z-L-Ala-α-AeMet(γ-Phth)-L-Ala-OtBu 
• 96971-34-5 N-Trityl-glycyl-alanin-tert.-butylester 
• 10068-63-0 Z-Lys(BOC)-Ala-OBut 
• 26054-99-9 N-Carbobenzoxy-L-asparaginyl-L-alanine tert-butyl ester 
• 258354-22-2 (S)-2-{[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-amino}-propionic acid tert-butyl ester 
• 136497-27-3 (S)-tert-butyl 2-((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanamido)propanoate 
• 33033-71-5 (S)-tert-butyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)propanoate 
• 269064-14-4 (S)-2-[(S)-2-[(Naphthalene-1-carbonyl)-amino]-3-(4-nitro-phenyl)-propionylamino]-propionic acid tert-butyl ester 
• 258354-21-1 tert-butyl (E)-N-(4-chlorobenzylidene)-L-alaninate 
• 669074-38-8 (S)-2-((S)-2-Fluoro-3-methyl-butyrylamino)-propionic acid tert-butyl ester 

Relevant academic research and scientific papers

Efficient and Divergent Total Synthesis of (-)-Epicoccin G and (-)-Rostratin A Enabled by Double C(sp3)-H Activation

Dithiodiketopiperazines are complex polycyclic natural products possessing a variety of interesting biological activities. Despite their interest, relatively few total syntheses have been completed. We herein report the enantioselective, scalable, and divergent total synthesis of two symmetrical pentacyclic dithiodiketopiperazines, (-)-epicoccin G and (-)-rostratin A. A common intermediate was synthesized on a multigram scale from inexpensive, commercially available starting materials using an enantioselective organocatalytic epoxidation and a double C(sp3)-H activation as key steps, with the latter allowing the efficient simultaneous construction of the two five-membered rings. In addition to the cis,cis-fused target (-)-epiccocin G, the more challenging (-)-rostratin A, possessing two trans ring junctions, was obtained for the first time on a 500 mg scale through the optimization of each step and validation on multigram quantities. Both natural products were synthesized with high overall yields (13-20%). This study should facilitate access to this fascinating and yet understudied family of biologically active natural products.

Stereoretentive N-Arylation of Amino Acid Esters with Cyclohexanones Utilizing a Continuous-Flow System

The N-arylation of chiral amino acid esters with minimal racemization is a challenging transformation because of the sensitivity of the α-stereocenter. A versatile synthetic method was developed to prepare N-arylated amino acid esters using cyclohexanones as aryl sources under continuous-flow conditions. The designed flow system, which consists of a coil reactor and a packed-bed reactor containing a Pd(OH)2/C catalyst, efficiently afforded the desired N-arylated amino acids without significant racemization, accompanied by only small amounts of easily removable co-products (i. e., H2O and alkanes). The efficiency and robustness of this method allowed for the continuous synthesis of the desired product in very high yield and enantiopurity with high space-time yield (74.1 g L?1 h?1) and turnover frequency (5.9 h?1) for at least 3 days.

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.

Asymmetric Synthesis of α-Amino Acids by Organocatalytic Biomimetic Transamination

A biomimetic enantioselective transamination of α-keto ester derivatives can be realized under mild conditions by using chiral quaternary ammonium arenecarboxylates in the absence of base additives. The corresponding α-amino acids can be used as versatile intermediates for further synthetic transformations that furnish chiral pyrrolidine and octahydroindolizine derivatives.

Challenges in the Development of a Thiol-Based Broad-Spectrum Inhibitor for Metallo-β-Lactamases

Pathogens, expressing metallo-β-lactamases (MBLs), become resistant against most β-lactam antibiotics. Besides the dragging search for new antibiotics, development of MBL inhibitors would be an alternative weapon against resistant bacterial pathogens. Inhibition of resistance enzymes could restore the antibacterial activity of β-lactams. Various approaches to MBL inhibitors are described; among others, the promising motif of a zinc coordinating thiol moiety is very popular. Nevertheless, since the first report of a thiol-based MBL inhibitor (thiomandelic acid) in 2001, no steps in development of thiol based MBL inhibitors were reported that go beyond clinical isolate testing. In this study, we report on the synthesis and biochemical characterization of thiol-based MBL inhibitors and highlight the challenges behind the development of thiol-based compounds, which exhibit good in vitro activity toward a broad spectrum of MBLs, selectivity against human off-targets, and reasonable activity against clinical isolates.

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.

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.

Rational design of an orthosteric regulator of hIAPP aggregation

Developing compounds regulating amyloid toxic oligomer but not fibril formation should constitute an effective strategy for the treatment of diabetes. Based on the full understanding of the folding mechanism, we designed an orthosteric helix regulator that can promote hIAPP to assemble into large non-cytotoxic oligomers. As a result, the islet cells were protected. This journal is

Peptide fragment coupling using a continuous-flow photochemical rearrangement of nitrones

Go with the flow: A general approach for amide bond formation by way of a continuous-flow photochemical rearrangement of nitrones was described (see scheme). Simple aryl-alkyl amide bonds as well as complex peptide bonds were constructed efficiently with a residence time less than 20minutes. A tetrapeptide was synthesized in this way and the method could be applied to peptide fragment coupling. Copyright

Asymmetric α-2-tosylethenylation of N,N-dialkyl-l-amino acid esters via the formation of non-racemic ammonium enolates

Asymmetric α-2-tosylethenylation of (S)-2-(pyrrolidin-1-yl)propanoic acid esters was shown to produce good yields with high enantioselectivities. The reaction proceeds via the formation of a non-racemic ammonium enolate without an external source of chirality.