82732-07-8

Basic information

• Product Name: Boc-D-homophenylalanine
• Synonyms: BOC-D-HOMOPHENYL-ALA;BOC-D-HOMOPHENYLALANINE;BOC-D-HOMOPHE-OH;BOC-D-HOPHE-OH;BOC-D-HFE-OH;BOC-HOMO-D-PHENYLALANINE;BOC-(R)-2-AMINO-4-PHENYLBUTYRIC ACID;2-tert-Butoxycarbonylamino-4-phenyl-butyric acid
• CAS NO: 82732-07-8
• Molecular Formula: C₁₅H₂₁NO₄
• Molecular Weight: 279.33
• Product Categories: Phenylalanine analogs and other aromatic alpha amino acids;Amino Acid Derivatives;PROTECTED AMINO ACID & PEPTIDES;Amino Acids
• Mol File: 82732-07-8.mol

Chemical Properties

• Melting Point: 71-78℃
• Boiling Point: 439.6 °C at 760 mmHg
• Flash Point: 219.7 °C
• Appearance: White to off-white/Powder
• Density: 1.139
• Storage Temp.: Store at 0°C
• PKA: 3.95±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• BRN: 3653505
• CAS DataBase Reference: Boc-D-homophenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-D-homophenylalanine(82732-07-8)
• EPA Substance Registry System: Boc-D-homophenylalanine(82732-07-8)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 82732-07-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Boc-D-homophenylalanine is used as a key intermediate for the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and dyes. Its unique structure allows for selective reactions and the formation of complex molecules with potential applications in different industries.
Used in Pharmaceutical Industry:
Boc-D-homophenylalanine is used as a building block for the development of novel drugs and therapeutic agents. Its chiral nature and reactivity make it an attractive candidate for the synthesis of enantiomerically pure compounds, which are essential for the pharmaceutical industry to ensure the desired biological activity and minimize side effects.
Used in Agrochemical Industry:
Boc-D-homophenylalanine is used as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides. Its unique structure can be utilized to create new molecules with improved efficacy and selectivity, leading to more effective and environmentally friendly products.
Used in Dye Industry:
Boc-D-homophenylalanine is used as a starting material for the production of dyes and pigments. Its homophenylalanine moiety can be modified to create a wide range of colors and properties, making it a valuable resource for the dye industry.

Upstream product

• 116696-85-6 (2S)-2-t-butoxycarbonylamino-3-phenylsulfonyl-1-(2-tetrahydropyranyloxy)propane 
• 116611-46-2 tert-butyl [(2R)-1-hydroxy-3-(tetrahydro-2H-pyran-2-yloxy)propan-2-yl]carbamate 
• 116611-63-3 methyl N-(tert-butoxycarbonyl)-O-(tetrahydro-2H-pyran-2-yl)-L-serinate 
• 116611-50-8 ((S)-2-Benzenesulfonyl-1-hydroxymethyl-ethyl)-carbamic acid tert-butyl ester 
• 116611-60-0 ((S)-2-Benzenesulfonyl-1-hydroxymethyl-3-phenyl-propyl)-carbamic acid tert-butyl ester 
• 116611-51-9 [(S)-2-Benzenesulfonyl-3-phenyl-1-(tetrahydro-pyran-2-yloxymethyl)-propyl]-carbamic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 943-73-7 D-homophenylalanine 
• 116611-45-1 (2R)-2-t-butoxycarbonylamino-3-phenylsulfonyl-1-(2-tetrahydropyranyloxy)propane 
• 116611-42-8 (R)-2-tert-butoxycarbonylamino-3-phenylsulfanylpropionic acid methyl ester 
• 116611-43-9 (R)-2-tert-butyl carbamoyl-1-hydroxy-3-(phenylthio)propane 
• 116611-44-0 ((R)-2-benzenesulfonyl-1-hydroxymethyl-ethyl)carbamic acid tert-butyl ester 
• 116611-60-0 ((R)-2-Benzenesulfonyl-1-hydroxymethyl-3-phenyl-propyl)-carbamic acid tert-butyl ester 
• 116611-51-9 [(R)-2-Benzenesulfonyl-3-phenyl-1-(tetrahydro-pyran-2-yloxymethyl)-propyl]-carbamic acid tert-butyl ester 

Downstream Products

• 254882-54-7 N-tert-butoxycarbonyl-D-homophenylalanine 3-quinolylamide 
• 171357-71-4 N-tert-butoxycarbonyl-homophenylalanine-N'-methoxy-N'-carboxamide 
• 1162084-31-2 C₁₆H₂₁N₃O₃ 
• 128779-46-4 N-tert-butoxycarbonyl-L-homophenylalanyl-L-cysteinyl(Acm)-D-tryptophyl-L-leucine methyl ester 

Relevant articles and documents

Fluorovinylsulfones and -Sulfonates as Potent Covalent Reversible Inhibitors of the Trypanosomal Cysteine Protease Rhodesain: Structure-Activity Relationship, Inhibition Mechanism, Metabolism, and in Vivo Studies

Rhodesain is a major cysteine protease of Trypanosoma brucei rhodesiense, a pathogen causing Human African Trypanosomiasis, and a validated drug target. Recently, we reported the development of α-halovinylsulfones as a new class of covalent reversible cysteine protease inhibitors. Here, α-fluorovinylsulfones/-sulfonates were optimized for rhodesain based on molecular modeling approaches. 2d, the most potent and selective inhibitor in the series, shows a single-digit nanomolar affinity and high selectivity toward mammalian cathepsins B and L. Enzymatic dilution assays and MS experiments indicate that 2d is a slow-tight binder (Ki = 3 nM). Furthermore, the nonfluorinated 2d-(H) shows favorable metabolism and biodistribution by accumulation in mice brain tissue after intraperitoneal and oral administration. The highest antitrypanosomal activity was observed for inhibitors with an N-terminal 2,3-dihydrobenzo[b][1,4]dioxine group and a 4-Me-Phe residue in P2 (2e/4e) with nanomolar EC50 values (0.14/0.80 μM). The different mechanisms of reversible and irreversible inhibitors were explained using QM/MM calculations and MD simulations.

N-ALKOXYAMIDE CONJUGATES AS IMAGING AGENTS

The present disclosure is directed to compounds, diagnostic agents, and related methods. In some cases, methods for treating patients are provided. More specifically, the disclosure provides compounds, diagnostic agents, and kits for detecting and/or imaging and/or monitoring elastin rich tissues. In addition, the disclosure provides methods of detecting and/or imaging and/or monitoring the presence of coronary plaque, carotid plaque, iliac/femoral plaque, aortic plaque, renal artery plaque, plaque of any arterial vessel, aneurism, vasculitis, other diseases of the arterial wall, and/or damage or structural changes in ligaments, uterus, lungs or skin, as indicated by changes in total vessel wall area, internal lumen size, and exterior arterial perimeter.

Quantum Chemical-Based Protocol for the Rational Design of Covalent Inhibitors

We propose a structure-based protocol for the development of customized covalent inhibitors. Starting from a known inhibitor, in the first and second steps appropriate substituents of the warhead are selected on the basis of quantum mechanical (QM) computations and hybrid approaches combining QM with molecular mechanics (QM/MM). In the third step the recognition unit is optimized using docking approaches for the noncovalent complex. These predictions are finally verified by QM/MM or molecular dynamic simulations. The applicability of our approach is successfully demonstrated by the design of reversible covalent vinylsulfone-based inhibitors for rhodesain. The examples show that our approach is sufficiently accurate to identify compounds with the desired properties but also to exclude nonpromising ones.

N-alkoxyamide conjugates as imaging agents

The present disclosure is directed to compounds, diagnostic agents, and related methods. In some cases, methods for treating patients are provided. More specifically, the disclosure provides compounds, diagnostic agents, and kits for detecting and/or imaging and/or monitoring elastin rich tissues. In addition, the disclosure provides methods of detecting and/or imaging and/or monitoring the presence of coronary plaque, carotid plaque, iliac/femoral plaque, aortic plaque, renal artery plaque, plaque of any arterial vessel, aneurism, vasculitis, other diseases of the arterial wall, and/or damage or structural changes in ligaments, uterus, lungs or skin, as indicated by changes in total vessel wall area, internal lumen size, and exterior arterial perimeter.

Development of novel dipeptide-like rhodesain inhibitors containing the 3-bromoisoxazoline warhead in a constrained conformation

Novel dipeptide-like rhodesain inhibitors containing the 3-bromoisoxazoline warhead in a constrained conformation were developed; some of them possess Ki values in the micromolar range. We studied the structure-activity relationship of these derivatives and we performed docking studies, which allowed us to find out the key interactions established by the inhibitors with the target enzyme. Biological results indicate that the nature of the P2 and P3 substituents and their binding to the S2/S3 pockets is strictly interdependent.

Synthesis of γ-oxo γ-aryl and γ-aryl α-amino acids from aromatic aldehydes and serine

γ-Oxo α-amino acids and γ-aryl α-amino acids are compounds with very interesting biological properties and are active components of many drug molecules. Oxo amino acids are also used as synthetic precursors for a number of unnatural amino acids and amino alcohols. We report a very efficient synthesis of such compounds through the coupling of aromatic dithianes, prepared from aromatic aldehydes and an iodide derivative of serine. The dithiane groups in compounds thus obtained can be either hydrolyzed or reduced to generate 4-oxo-4-aryl or 4-aryl 2-amino butanol derivatives, respectively, which, on further transformations, can be converted into the title compounds. Starting with L-serine provides the corresponding D-amino acids with complete enantiopurity. The reported method is economically viable and complements the existing methods, which rely largely on cross-coupling reactions.

N-ALKOXYAMIDE CONJUGATES AS IMAGING AGENTS

The present disclosure is directed to compounds, diagnostic agents, and related methods. In some cases, methods for treating patients are provided. More specifically, the disclosure provides compounds, diagnostic agents, and kits for detecting and/or imaging and/or monitoring elastin rich tissues. In addition, the disclosure provides methods of detecting and/or imaging and/or monitoring the presence of coronary plaque, carotid plaque, iliac/femoral plaque, aortic plaque, renal artery plaque, plaque of any arterial vessel, aneurism, vasculitis, other diseases of the arterial wall, and/or damage or structural changes in ligaments, uterus, lungs or skin, as indicated by changes in total vessel wall area, internal lumen size, and exterior arterial perimeter.

HYDRAZIDE CONJUGATES AS IMAGING AGENTS

The present disclosure is directed to diagnostic agents. More specifically, the disclosure is directed to compounds, diagnostic agents, compositions, and kits for detecting and/or imaging and/or monitoring a pathological disorder associated with coronary plaque, carotid plaque, aortic plaque, plaque of the arterial vessel, aneurism, vasculitis, and other diseases of the arterial wall. In addition, the disclosure is directed to methods of detecting and/or imaging and/or monitoring changes in the arterial wall, including expansive and constrictive remodeling, total vessel wall area, internal lumen size, and exterior artery perimeter.

Palladium-catalyzed cross-coupling reactions in one-pot multicatalytic processes

Palladium-catalyzed cross-coupling reactions have been investigated in multicatalytic processes to synthesize disubstituted alkenes and alkanes from carbonyl derivatives. The use of copper-catalyzed methylenation reactions is the key starting reaction to produce terminal alkenes which are not isolated, but submitted to further structure elongation. Not only is the isolation of the alkene intermediate unnecessary, but also the copper catalyst is a beneficial cocatalyst in the palladium-catalyzed cross-coupling reactions. The desired products are thus typically obtained in higher yields using this one-pot approach. We have used these processes to synthesize hydroxylated (E)-stilbenoids, which are known chemopreventive and chemotherapeutic agents, odorant-substituted indanes, and non-natural amino acids, such as homophenylalanine.

Vinylsulfones versus alkylsulfones in the addition to chiral imines. Synthesis of N-(tert-butoxycarbonyl)-L-homophenylalanine

A study of the addition of vinylsulfones versus alkylsufones has been done, and applied to the synthesis of N-(tert-butoxycarbonyl)-L-homophenylalanine.