220587-29-1

Basic information

• Product Name: (S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate
• Synonyms: (S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate;Methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanoate;L-Phenylalanine, N-[(1,1-diMethylethoxy)carbonyl]-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-, Methyl ester;2-(tert-butoxycarbonylamino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate;N-Boc-(3S,4S)-4-amino-3-hydroxy-5-phenyl pentanoic acid;methyl(S)-2-((tert-butoxycarbonyl)amino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate;4-[[9H-fluoren-9-ylmethoxy(oxo)methyl]amino]-3-hydroxy-5-phenylpentanoic acid;N-Boc-(3S,4S)-AHPPA
• CAS NO: 220587-29-1
• Molecular Formula: C₂₁H₃₂BNO₆
• Molecular Weight: 405.29
• Mol File: 220587-29-1.mol

Chemical Properties

• Boiling Point: 521.897 °C at 760 mmHg
• Flash Point: 269.434 °C
• Appearance: /
• Density: 1.10
• Storage Temp.: 2-8°C
• PKA: 10.96±0.46(Predicted)
• CAS DataBase Reference: (S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate(220587-29-1)
• EPA Substance Registry System: (S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate(220587-29-1)

Safety Data

• Hazardous Substances Data: 220587-29-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate is used as a synthetic intermediate for the preparation of complex organic molecules, leveraging its diverse functional groups to facilitate multiple reaction pathways and the construction of intricate molecular architectures.
Used in Medicinal Chemistry:
In the pharmaceutical industry, (S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate is used as a building block for the development of novel drug candidates. Its unique structure and functional groups may contribute to the design of new therapeutic agents with specific biological activities, potentially targeting various diseases and medical conditions.
Used in Materials Science:
(S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate is utilized in the development of advanced materials with tailored properties. Its incorporation into polymers, coatings, or other material systems can enhance performance characteristics such as stability, reactivity, or selectivity in various applications.

Upstream product

• 112766-18-4 methyl N-(tert-butoxycarbonyl)-O-[(trifluoromethyl)sulfonyl]-L-tyrosinate 
• 113850-76-3 N-(tert-butoxycarbonyl)-4-iodo-L-phenylalanine methyl ester 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 4326-36-7 (S)-N-(tert-butoxycarbonyl)tyrosine methyl ester 
• 103882-09-3 N-Boc-4-I-Phe-OH 
• 175844-11-8 methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-bromopropionate 
• 68716-49-4 p-bromophenylboronic acid pinacol ester 
• 69942-12-7 N-tert-butoxycarbonylserine methyl ester 
• 99359-33-8 (S)-methyl 2-amino-3-(4-bromophenyl)propanoate 
• 24250-84-8 H-p-BrPhe-OH 
• 63-91-2 L-phenylalanine 

Downstream Products

• 554418-80-3 methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(3-quinolinyl)phenyl]propionate 
• 216439-76-8 (S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate 
• 119771-23-2 N-(tert-butoxycarbonyl)-4-(dihydroxyboryl)-1-phenylalanine 
• 156017-43-5 (2S)-{4-[2-tert-butoxycarbonylamino-2-(methoxycarbonyl)-ethyl]-phenyl}difluoromethyl-phosphonic acid diethyl ester 
• 224824-22-0 (S)-(4-(2-((tert-butoxycarbonyl)amino)-3-methoxy-3-oxopropyl)phenyl)boronic acid 
• 401906-12-5 methyl N-(tert-butoxycarbonyl)-4-(3-methyl-2,6-dioxo-3,6-dihydropyrimidine-1(2H)-yl)-L-phenylalaninate 

Relevant articles and documents

Enantioselective synthesis of 4-substituted phenylalanines by cross- coupling reactions

The enantiomerically enriched BOC-protected (4- pinacolylborono)phenylalanine methyl ester (8) is produced via enzymatic resolution of the racemic material, or direct synthesis from the corresponding iodide (or triflate), and undergoes Suzuki-Miyaura coup

Rhodium-Catalyzed Dealkenylative Arylation of Alkenes with Arylboronic Compounds

The C?C bond formation reaction represents a fundamental and important transformation in synthetic chemistry, and exploring new types of C?C bond formation reactions is recognized as appealing, yet challenging. Herein, we disclose the first example of rhodium-catalyzed dealkenylative arylation of alkenes with arylboronic compounds, thereby providing an unconventional access to bi(hetero)aryls with excellent chemoselectivity. In this method, C(aryl)?C(alkenyl) and C(alkenyl)?C(alkenyl) bonds in various alkenes and 1,3-dienes can be cleaved via a hydrometalation and followed by β-carbon elimination pathway for Suzuki–Miyaura reactions. Furthermore, a series of novel organic fluorescent molecules with excellent photophysical properties has been efficiently constructed with this protocol.

Synthesis of Enantiopure Unnatural Amino Acids by Metallaphotoredox Catalysis

We describe herein a two-step process for the conversion of serine to a wide array of optically pure unnatural amino acids. This method utilizes a photocatalytic cross-electrophile coupling between a bromoalkyl intermediate and a diverse set of aryl halides to produce artificial analogues of phenylalanine, tryptophan, and histidine. The reaction is tolerant of a broad range of functionalities and can be leveraged toward the scalable synthesis of valuable pharmaceutical scaffolds via flow technology.

ANTIMICROBIAL COMPOUNDS AND METHODS

The invention is directed to compounds that are active as antibacterial agents. The invention compounds are active against gram-positive and gram-negative bacteria and can be used to treat infections caused by gram-positive and gram-negative bacteria. Also disclosed are processes and intermediates for making the compounds.

Process Development of Tryptophan Hydroxylase Inhibitor LX1031, a Drug Candidate for the Treatment of Irritable Bowel Syndrome

Two process routes for LX1031, a tryptophan hydroxylase inhibitor for the treatment of irritable bowel syndrome, were developed. They shared the same left-hand and right-hand starting materials as well as the penultimate intermediate. The chiral center in

P(III)/P(V)-Catalyzed Methylamination of Arylboronic Acids and Esters: Reductive C-N Coupling with Nitromethane as a Methylamine Surrogate

The direct reductive N-arylation of nitromethane by organophosphorus-catalyzed reductive C-N coupling with arylboronic acid derivatives is reported. This method operates by the action of a small ring organophosphorus-based catalyst (1,2,2,3,4,4-hexamethylphosphetane P-oxide) together with a mild terminal reductant hydrosilane to drive the selective installation of the methylamino group to (hetero)aromatic boronic acids and esters. This method also provides for a unified synthetic approach to isotopically labeled N-methylanilines from various stable isotopologues of nitromethane (i.e., CD3NO2, CH315NO2, and 13CH3NO2), revealing this easy-to-handle compound as a versatile precursor for the direct installation of the methylamino group.

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.

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.

INTEGRIN ANTAGONISTS

The present disclosure provides therapeutic agents including those of the formula: wherein the variables are defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such therapeutic agents. Methods of using the therapeutic agents are also provided.

SULFONAMIDE DERIVATIVE AND PHARMACEUTICAL USE THEREOF

Provided is a sulfonamide derivative represented by the following general formula (1) and having an α4 integrin inhibitory effect with high selectivity with a low effect on α4β1 and a high effect on α4β7, or a pharmaceutically acceptable salt thereof (in the general formula (1), A, B, D, E, R41, and a to h are as described in the description).