210962-91-7

Usage

Uses

Used in Pharmaceutical Industry:
METHYL (R)-2-(TERT-BUTOXYCARBONYLAMINO)-3-(4-IODOPHENYL)PROPANOATE is used as a building block for the synthesis of peptide molecules, which are essential components of various pharmaceuticals and medications. Its unique structure and properties make it a valuable asset in the development of new drugs and medications.
Used in Research Chemicals:
METHYL (R)-2-(TERT-BUTOXYCARBONYLAMINO)-3-(4-IODOPHENYL)PROPANOATE is also used in the preparation of research chemicals, where it serves as a key component in the synthesis of various compounds. Its versatility and reactivity make it an important tool for researchers in the field of chemistry and pharmaceuticals.

Upstream product

• 186581-53-3 diazomethane 
• 103882-09-3 N-Boc-4-I-Phe-OH 
• 34619-03-9 tert-butyldicarbonate 
• 62561-75-5 (R)-2-amino-3-(4-iodophenyl)propanoic acid 
• 76757-90-9 N-(tert-butoxycarbonyl)-D-tyrosine methyl ester 
• 103882-09-3 N-Boc-DL-4-iodophenylalanine 
• 74-88-4 methyl iodide 
• 1991-81-7 p-iodophenylalanine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 673-06-3 D-(R)-phenylalanine 
• 372967-43-6 (R)-methyl 2-amino-3-(4-iodophenyl)propanoate 
• 67-56-1 methanol 
• 63-91-2 L-phenylalanine 
• 1991-81-7 4-iodo-L-phenylalanine 

Downstream Products

• 156017-43-5 (2S)-{4-[2-tert-butoxycarbonylamino-2-(methoxycarbonyl)-ethyl]-phenyl}difluoromethyl-phosphonic acid diethyl ester 
• 137255-86-8 methyl (S)-3-([1,1'-biphenyl]-4-yl)-2-((tert-butoxycarbonyl)amino)propanoate 
• 1501940-85-7 ((4-methoxyphenyl)((4-(S)-2-(di-tert-butoxycarbonyl)amino)-3-oxo-3-methoxypropyl)phenyl)(trifluoromethanesulfonyl)-λ³-iodane 

Relevant academic research and scientific papers

Preparation method of sacubitril intermediate

The invention relates to the technical field of synthesis of medical intermediates, in particular to a preparation method of a sacubitril intermediate, which comprises the following steps: 1) reacting a raw material compound III with phosphorus trihalide to obtain a compound II; and 2) reacting the compound II with phenylhydrazine in the presence of a catalyst and an additive to obtain a sacubitril intermediate, namely a compound I. According to the invention, cheap phosphorus trihalide is selected to replace expensive and highly toxic trifluoromethanesulfonic anhydride, and cheap phenylhydrazine and a catalyst palladium chloride are adopted. The method has the advantages of simple reaction operation, low cost and high yield, and is easier for industrial production of the compound I.

Nickel-Catalyzed Asymmetric Synthesis of α-Arylbenzamides

A nickel-catalyzed asymmetric reductive hydroarylation of vinyl amides to produce enantioenriched α-arylbenzamides is reported. The use of a chiral bisimidazoline (BIm) ligand, in combination with diethoxymethylsilane and aryl halides, enables the regioselective introduction of aryl groups to the internal position of the olefin, forging a new stereogenic center α to the N atom. The use of neutral reagents and mild reaction conditions provides simple access to pharmacologically relevant motifs present in anticancer, SARS-CoV PLpro inhibitors, and KCNQ channel openers.

Total Synthesis of Seongsanamide B

The first total synthesis of the bicyclic depsipeptide natural product seongsanamide B is described. The successful approach employed solid-phase peptide synthesis of a core heptapeptide, incorporating on-resin esterification, followed by solution-phase macrolactamization and a late stage intramolecular Evans-Chan-Lam coupling to generate the biaryl ether of the isodityrosine unit.

Facile synthesis of a novel genetically encodable fluorescent α-amino acid emitting greenish blue light

We report the facile synthesis and characterization of a novel fluorescent α-amino acid 4-phenanthracen-9-yl-l-phenylalanine (Phen-AA) (5) that emits greenish blue light in the visible region. This genetically encodable l-α-amino acid has excellent photostability with a 75% quantum yield. It readily gets into human cells, being clearly imaged upon 405 nm laser excitation. The synthetic procedure is resistant to racemization and only involves three simple steps which use mild conditions and generate the Phen-AA in reasonably good yield. It may find broad applications in research, biotechnology, and the pharmaceutical industry.

Sequence Programming with Dynamic Boronic Acid/Catechol Binary Codes

The development of a synthetic code that enables a sequence programmable feature like DNA represents a key aspect toward intelligent molecular systems. We developed herein the well-known dynamic covalent interaction between boronic acids (BAs) and catechols (CAs) into synthetic nucleobase analogs. Along a defined peptide backbone, BA or CA residues are arranged to enable sequence recognition to their complementary strand. Dynamic strand displacement and errors were elucidated thermodynamically to show that sequences are able to specifically select their partners. Unlike DNA, the pH dependency of BA/CA binding enables the dehybridization of complementary strands at pH 5.0. In addition, we demonstrate the sequence recognition at the macromolecular level by conjugating the cytochrome c protein to a complementary polyethylene glycol chain in a site-directed fashion.

Electron-deficient p-benzoyl-l-phenylalanine derivatives increase covalent chemical capture yields for protein–protein interactions

The photoactivatable amino acid p-benzoyl-l-phenylalanine (pBpa) has been used for the covalent capture of protein–protein interactions (PPIs) in vitro and in living cells. However, this technique often suffers from poor photocrosslinking yields due to th

Electrochemical synthesis of 1,2-diketones from alkynes under transition-metal-catalyst-free conditions

We report an electrochemical protocol for the direct oxidation of internal alkynes in air to provide 1,2-diketones. A variety of functional groups and heterocycle-containing substrates can be tolerated well under mild conditions.

Photoinduced Hydroxylation of Organic Halides under Mild Conditions

Presented in this paper is photoinduced hydroxylation of organic halides, providing a mild access to a range of functionalized phenols and aliphatic alcohols. These reactions generally proceed under mild reaction conditions with no need for a photocatalyst or a strong base and show a wide substrate scope as well as excellent functional group tolerance. This work highlights the unique role of NaI that allows a challenging transformation to proceed under mild reaction conditions.

Solid-phase synthesis of biaryl bicyclic peptides containing a 3-aryltyrosine or a 4-arylphenylalanine moiety

A methodology for the solid-phase synthesis of biaryl bicyclic peptides containing a Phe-Phe, a Phe-Tyr or a Tyr-Tyr motif has been devised. This approach comprises two key steps. The first one involves the cyclization of a linear peptidyl resin containing the corresponding halo- and boronoamino acids via a microwave-assisted Suzuki–Miyaura cross coupling. This step is followed by the macrolactamization of the resulting biaryl monocyclic peptidyl resin leading to the formation of the expected biaryl bicyclic peptide. This study provides the first solid-phase synthesis of this type of bicyclic compounds being amenable to prepare a diversity of synthetic or natural biaryl bicyclic peptides.

A Bifunctional Amino Acid Enables Both Covalent Chemical Capture and Isolation of in Vivo Protein–Protein Interactions

In vivo covalent chemical capture by using photoactivatable unnatural amino acids (UAAs) is a powerful tool for the identification of transient protein–protein interactions (PPIs) in their native environment. However, the isolation and characterization of