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BOC-D-Phenylalanine is the BOC (tert-butyloxycarbonyl) protected form of D-phenylalanine. It can be used in the synthesis of benzo[de][1,7] napthyridinones as PARP1 inhibitors. It is also an important reagent during the manufacturing of proline-containing, ?-turn mimetic cycle tetrapeptides.

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  • 18942-49-9 Structure
  • Basic information

    1. Product Name: BOC-D-PHE-OH
    2. Synonyms: BOC-D-PHE;BOC-D-PHE-OH;BOC-D-PHENYLALANINE;(R)-2-TERT-BUTOXYCARBONYLAMINO-3-PHENYL-PROPIONIC ACID;N-T-BOC-D-PHENYLALANINE;N-(TERT-BUTOXYCARBONYL)-D-PHENYLALANINE;Boc-D-Phe-OH >=99.0% (sum of enantiomers, TLC);Boc-D-phenylalanine≥ 99% (HPLC)
    3. CAS NO:18942-49-9
    4. Molecular Formula: C14H19NO4
    5. Molecular Weight: 265.3
    6. EINECS: 1533716-785-6
    7. Product Categories: Amino Acids;Phenylalanine [Phe, F];Boc-Amino Acids and Derivative;Amino Acids (N-Protected);Biochemistry;Boc-Amino Acids;Boc-Amino acid series
    8. Mol File: 18942-49-9.mol
    9. Article Data: 50
  • Chemical Properties

    1. Melting Point: 78-87 °C
    2. Boiling Point: 408.52°C (rough estimate)
    3. Flash Point: 211.8 °C
    4. Appearance: White/Fine Crystalline Powder
    5. Density: 1.1356 (rough estimate)
    6. Vapor Pressure: 4.88E-08mmHg at 25°C
    7. Refractive Index: -25 ° (C=1, EtOH)
    8. Storage Temp.: 2-8°C
    9. Solubility: DMSO, Ethanol, Methanol
    10. PKA: 3.88±0.10(Predicted)
    11. Water Solubility: insoluble
    12. BRN: 3593396
    13. CAS DataBase Reference: BOC-D-PHE-OH(CAS DataBase Reference)
    14. NIST Chemistry Reference: BOC-D-PHE-OH(18942-49-9)
    15. EPA Substance Registry System: BOC-D-PHE-OH(18942-49-9)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: N/A
    3. Safety Statements: 24/25
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 18942-49-9(Hazardous Substances Data)

18942-49-9 Usage

Chemical Properties

white fine crystalline powder

Uses

Different sources of media describe the Uses of 18942-49-9 differently. You can refer to the following data:
1. Boc-D-Phenylalanine is used in the synthesis of benzo[de][1,7]napthyridinones as PARP1 inhibitors. Also it is an important reagent in the preparation of proline-containing, β-turn mimetic cycle tetrap eptides.
2. Boc-D-Phenylalanine is used in the synthesis of benzo[de][1,7]napthyridinones as PARP1 inhibitors. Also it is an important reagent in the preparation of proline-containing, β-turn mimetic cycle tetrapeptides.

References

https://www.clearsynth.com/en/CST07663.html http://www.biocompare.com/Protein-Biochemistry/10318-Boc-Protected-Phenylalanine-Monomers-and-Derivatives/

Check Digit Verification of cas no

The CAS Registry Mumber 18942-49-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,8,9,4 and 2 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 18942-49:
(7*1)+(6*8)+(5*9)+(4*4)+(3*2)+(2*4)+(1*9)=139
139 % 10 = 9
So 18942-49-9 is a valid CAS Registry Number.
InChI:InChI=1/C14H19NO4/c1-14(2,3)19-13(18)15-11(12(16)17)9-10-7-5-4-6-8-10/h4-8,11H,9H2,1-3H3,(H,15,18)(H,16,17)/p-1/t11-/m1/s1

18942-49-9 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Detail
  • TCI America

  • (B2989)  N-(tert-Butoxycarbonyl)-D-phenylalanine  >98.0%(T)

  • 18942-49-9

  • 5g

  • 440.00CNY

  • Detail
  • TCI America

  • (B2989)  N-(tert-Butoxycarbonyl)-D-phenylalanine  >98.0%(T)

  • 18942-49-9

  • 25g

  • 1,290.00CNY

  • Detail
  • Alfa Aesar

  • (L08722)  N-Boc-D-phenylalanine, 98%   

  • 18942-49-9

  • 1g

  • 210.0CNY

  • Detail
  • Alfa Aesar

  • (L08722)  N-Boc-D-phenylalanine, 98%   

  • 18942-49-9

  • 5g

  • 761.0CNY

  • Detail
  • Aldrich

  • (15484)  Boc-D-Phe-OH  ≥99.0% (sum of enantiomers, TLC)

  • 18942-49-9

  • 15484-5G

  • 651.69CNY

  • Detail

18942-49-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoic acid

1.2 Other means of identification

Product number -
Other names (R)-N-(tert-butoxycarbonyl)phenylalanine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:18942-49-9 SDS

18942-49-9Relevant articles and documents

Enantiomeric discrimination of α-hydroxy acids and N-Ts-α-amino acids by1H NMR spectroscopy

Gao, Guangpeng,Lv, Caixia,Li, Qiuju,Ai, Lin,Zhang, Jiaxin

, p. 6742 - 6746 (2015)

A new kind of chiral compounds with multiple amino, amido and phenolic hydroxy groups has been synthesized from D-phenylalanine and D-phenylglycine, respectively. The enantiomeric discriminations of α-hydroxy acids and N-Ts-α-amino acids have been finished in the presence of the above chiral compounds as chiral solvating agents by1H NMR spectroscopy. The results show that the chiral compounds are highly effective and practical chiral solvating agents towards α-hydroxy acids and N-Ts-α-amino acids.

Synthesis and Biological Evaluation of PSMA Ligands with Aromatic Residues and Fluorescent Conjugates Based on Them

Machulkin, Aleksei E.,Shafikov, Radik R.,Uspenskaya, Anastasia A.,Petrov, Stanislav A.,Ber, Anton P.,Skvortsov, Dmitry A.,Nimenko, Ekaterina A.,Zyk, Nikolay U.,Smirnova, Galina B.,Pokrovsky, Vadim S.,Abakumov, Maxim A.,Saltykova, Irina V.,Akhmirov, Rauf T.,Garanina, Anastasiia S.,Polshakov, Vladimir I.,Saveliev, Oleg Y.,Ivanenkov, Yan A.,Aladinskaya, Anastasiya V.,Finko, Alexander V.,Yamansarov, Emil U.,Krasnovskaya, Olga O.,Erofeev, Alexander S.,Gorelkin, Petr V.,Dontsova, Olga A.,Beloglazkina, Elena K.,Zyk, Nikolay V.,Khazanova, Elena S.,Majouga, Alexander G.

supporting information, p. 4532 - 4552 (2021/05/06)

Prostate-specific membrane antigen (PSMA), also known as glutamate carboxypeptidase II (GCPII), is a suitable target for specific delivery of antitumor drugs and diagnostic agents due to its overexpression in prostate cancer cells. In the current work, we describe the design, synthesis, and biological evaluation of novel low-molecular PSMA ligands and conjugates with fluorescent dyes FAM-5, SulfoCy5, and SulfoCy7. In vitro evaluation of synthesized PSMA ligands on the activity of PSMA shows that the addition of aromatic amino acids into a linker structure leads to a significant increase in inhibition. The conjugates of the most potent ligand with FAM-5 as well as SulfoCy5 demonstrated high affinities to PSMA-expressing tumor cells in vitro. In vivo biodistribution in 22Rv1 xenografts in Balb/c nude mice of PSMA-SulfoCy5 and PSMA-SulfoCy7 conjugates with a novel PSMA ligand demonstrated good visualization of PSMA-expressing tumors. Also, the conjugate PSMA-SulfoCy7 demonstrated the absence of any explicit toxicity up to 87.9 mg/kg.

Novel irreversible covalent BTK inhibitors discovered using DNA-encoded chemistry

Guilinger, John P.,Archna, Archna,Augustin, Martin,Bergmann, Andreas,Centrella, Paolo A.,Clark, Matthew A.,Cuozzo, John W.,D?ther, Maike,Guié, Marie-Aude,Habeshian, Sevan,Kiefersauer, Reiner,Krapp, Stephan,Lammens, Alfred,Lercher, Lukas,Liu, Julie,Liu, Yanbin,Maskos, Klaus,Mrosek, Michael,Pflügler, Klaus,Siegert, Markus,Thomson, Heather A.,Tian, Xia,Zhang, Ying,Konz Makino, Debora L.,Keefe, Anthony D.

supporting information, (2021/06/15)

Libraries of DNA-Encoded small molecules created using combinatorial chemistry and synthetic oligonucleotides are being applied to drug discovery projects across the pharmaceutical industry. The majority of reported projects describe the discovery of reve

Identification and Profiling of a Novel Diazaspiro[3.4]octane Chemical Series Active against Multiple Stages of the Human Malaria Parasite Plasmodium falciparum and Optimization Efforts

Le Manach, Claire,Dam, Jean,Woodland, John G.,Kaur, Gurminder,Khonde, Lutete P.,Brunschwig, Christel,Njoroge, Mathew,Wicht, Kathryn J.,Horatscheck, André,Paquet, Tanya,Boyle, Grant A.,Gibhard, Liezl,Taylor, Dale,Lawrence, Nina,Yeo, Tomas,Mok, Sachel,Eastman, Richard T.,Dorjsuren, Dorjbal,Talley, Daniel C.,Guo, Hui,Simeonov, Anton,Reader, Janette,Van Der Watt, Mari?tte,Erlank, Erica,Venter, Nelius,Zawada, Jacek W.,Aswat, Ayesha,Nardini, Luisa,Coetzer, Theresa L.,Lauterbach, Sonja B.,Bezuidenhout, Belinda C.,Theron, Anjo,Mancama, Dalu,Koekemoer, Lizette L.,Birkholtz, Lyn-Marie,Wittlin, Sergio,Delves, Michael,Ottilie, Sabine,Winzeler, Elizabeth A.,Smith, Dennis,Fidock, David A.,Street, Leslie J.,Basarab, Gregory S.,Duffy, James,Chibale, Kelly

supporting information, p. 2291 - 2309 (2021/03/01)

A novel diazaspiro[3.4]octane series was identified from a Plasmodium falciparum whole-cell high-throughput screening campaign. Hits displayed activity against multiple stages of the parasite lifecycle, which together with a novel sp3-rich scaffold provided an attractive starting point for a hit-to-lead medicinal chemistry optimization and biological profiling program. Structure-activity-relationship studies led to the identification of compounds that showed low nanomolar asexual blood-stage activity (50 nM) together with strong gametocyte sterilizing properties that translated to transmission-blocking activity in the standard membrane feeding assay. Mechanistic studies through resistance selection with one of the analogues followed by whole-genome sequencing implicated the P. falciparum cyclic amine resistance locus in the mode of resistance.

Highly Stable Zr(IV)-Based Metal-Organic Frameworks for Chiral Separation in Reversed-Phase Liquid Chromatography

Jiang, Hong,Yang, Kuiwei,Zhao, Xiangxiang,Zhang, Wenqiang,Liu, Yan,Jiang, Jianwen,Cui, Yong

supporting information, p. 390 - 398 (2021/01/13)

Separation of racemic mixtures is of great importance and interest in chemistry and pharmacology. Porous materials including metal-organic frameworks (MOFs) have been widely explored as chiral stationary phases (CSPs) in chiral resolution. However, it remains a challenge to develop new CSPs for reversed-phase high-performance liquid chromatography (RP-HPLC), which is the most popular chromatographic mode and accounts for over 90% of all separations. Here we demonstrated for the first time that highly stable Zr-based MOFs can be efficient CSPs for RP-HPLC. By elaborately designing and synthesizing three tetracarboxylate ligands of enantiopure 1,1′-biphenyl-20-crown-6, we prepared three chiral porous Zr(IV)-MOFs with the framework formula [Zr6O4(OH)8(H2O)4(L)2]. They share the same flu topological structure but channels of different sizes and display excellent tolerance to water, acid, and base. Chiral crown ether moieties are periodically aligned within the framework channels, allowing for stereoselective recognition of guest molecules via supramolecular interactions. Under acidic aqueous eluent conditions, the Zr-MOF-packed HPLC columns provide high resolution, selectivity, and durability for the separation of a variety of model racemates, including unprotected and protected amino acids and N-containing drugs, which are comparable to or even superior to several commercial chiral columns for HPLC separation. DFT calculations suggest that the Zr-MOF provides a confined microenvironment for chiral crown ethers that dictates the separation selectivity.

Structure-Activity Relationship Study of Majusculamides A and B and Their Analogues on Osteogenic Activity

Nakajima, Daisuke,Natsume, Noriyuki,Ozaki, Kaori,Teruya, Toshiaki,Yokoshima, Satoshi

supporting information, p. 2477 - 2482 (2020/10/02)

We discovered that majusculamide A (1) and majusculamide B (2), isolated from a marine cyanobacterium collected in Okinawa, induced osteoblast differentiation in MC3T3-E1 cells. Although majusculamide A (1) has a different configuration only at the C-19 stereocenter, bearing a methyl group, compared to majusculamide B (2), the effect of 1 was stronger than that of 2. We synthesized some analogues of the majusculamides (3-15) and evaluated osteogenic activities of these analogues. The structure-activity relationship study of majusculamide analogues suggested that the number of methyls and configuration at C-19 and the nature of the substituent at C-20 of majusculamide A (1) may be important for the osteoblast differentiation-inducing effect of 1.

Influence of the dipeptide linker configuration on the activity of PSMA ligands

Uspenskaya, Anastasiya A.,Machulkin, Alexey E.,Nimenko, Ekaterina A.,Shafikov, Radik R.,Petrov, Stanislav A.,Skvortsov, Dmitry A.,Beloglazkina, Elena K.,Majouga, Alexander G.

, p. 756 - 759 (2021/01/12)

Selective ligands of an urea-based prostate specific membrane antigen with a phenylalanine/tyrosine-based dipeptide linker and with a mingled chiral centers configuration and/or substituted aromatic fragments were prepared in seven steps by liquid- and in

DIHYDROPYRIMIDINE COMPOUNDS AND USES THEREOF IN MEDICINE

-

Paragraph 00237, (2019/05/10)

Provided herein are a dihydropyrimidine compound and use as a medicament, especially application as a medicament used for treating and preventing hepatitis B. Specifically, provided herein is a compound having Formula (I) or (Ia), or a stereisomer, a tautomer, an N-oxide, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof, wherein the variables of the formulas are as defined in the specification. Also provided herein is use of the compound having Formula (I) or (Ia), or an enantiomer, a diastereoisomer, a tautomer, a hydrate, a solvate, or a pharmaceutically acceptable salt thereof as a medicament, especially use as a medicament for treating and preventing hepatitis B.

Dihydropyridine compound and application thereof to drugs

-

Paragraph 0573; 0574; 0575; 0576, (2019/05/08)

The invention relates to a dihydropyridine compound and application of the dihydropyridine compound serving as a drug, in particular to application of the dihydropyridine compound serving as a drug for treating and preventing hepatitis B. Specifically, the invention relates to the compound shown as the general formula (I) or (Ia) (please see the specifications for the general formula (I) or (Ia))or stereoisomers, tautomer, a nitrogen oxide, solvate, metabolites and medically acceptable salt of the compound or a prodrug of the compound, wherein all variables are defined in the specification. The invention further relates to application of the compound shown as the general formula (I) or (Ia) or enantiomers, non-enantiomers, the tautomer, hydrates, the solvate or the medically acceptable salt of the compound serving as drugs, in particular to application of the compound or the enantiomers, the non-enantiomers, the tautomer, the hydrates, the solvate or the medically acceptable salt of the compound serving as the drugs for treating and preventing hepatitis B.

Total syntheses of cathepsin D inhibitory izenamides A, B, and C and structural confirmation of izenamide B

Lim, Changjin

, (2019/10/02)

The first total syntheses of izenamides A, B, and C, which are depsipeptides inhibitor of cathepsin D, were accomplished. In addition, the stereochemistry of izenamide B was confirmed by our syntheses. The key features of our synthetic route involve the avoidance of critical 2,5-diketopiperazine (DKP) formation and the minimization of epimerization during the coupling of amino acids for the target peptides.

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