Boc-D-phenylalanine

Base Information

• Chemical Name: Boc-D-phenylalanine
• CAS No.: 18942-49-9
• Molecular Formula: C14H19NO4
• Molecular Weight: 265.309
• Hs Code.: 29242990
• DSSTox Substance ID: DTXSID50348469
• Nikkaji Number: J814.363C
• Wikidata: Q72450259
• Mol file: 18942-49-9.mol

Synonyms:Boc-D-Phe-OH;Boc-D-phenylalanine;18942-49-9;N-Boc-D-phenylalanine;N-(tert-Butoxycarbonyl)-D-phenylalanine;(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoic acid;d-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-;MFCD00063149;(R)-2-(TERT-BUTOXYCARBONYLAMINO)-3-PHENYLPROPANOIC ACID;BocDPheOH;Boc-D-PheOH;Boc-DPhe-OH;Boc-D-phenyl-alanine;N-Boc-D-Phe;Boc-(D)Phe-OH;BOC-D-PHE;(TERT-BUTOXYCARBONYL)-D-PHENYLALANINE;SCHEMBL606309;t-butoxycarbonyl-D-phenylalanine;DTXSID50348469;(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-phenylpropanoic acid;tert-butyloxycarbonyl-d-phenylalanine;tert.-butoxycarbonyl-D-phenylalanine;N-(t-Butoxycarbonyl)-D-phenylalanine;AKOS015888245;AKOS015924106;AM82156;CS-W010128;HY-W009412;N-(tert-Butoxycarbonyl)phenylalanine #;N-tert-butyloxycarbonyl-D-phenylalanine;DS-13505;N-tert-butoxycarbonyl-beta-phenyl-D-alanine;B2989;N-alpha-tert-Butyloxycarbonyl-D-phenylalanine;EN300-35010;M03311;A813323;(R)-tert-butoxycarbonylamino-3-phenyl-propionic acid;J-300206;Q-101753;Boc-D-Phe-OH, >=99.0% (sum of enantiomers, TLC);(2R)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid;(2R)-2-tert-butoxycarbonylamino-3-phenylpropionic acid;Z285139170;2-(tert-butoxycarbonylamino)-3-phenyl-propanoate

Chemical Property of Boc-D-phenylalanine

Chemical Property:

• Appearance/Colour: white fine crystalline powder
• Vapor Pressure: 4.88E-08mmHg at 25°C
• Melting Point: 78-87 °C
• Refractive Index: -25 ° (C=1, EtOH)
• Boiling Point: 426.6 °C at 760 mmHg
• PKA: 3.88±0.10(Predicted)
• Flash Point: 211.8 °C
• PSA: 75.63000
• Density: 1.16 g/cm³
• LogP: 2.59790
• Storage Temp.: 2-8°C
• Solubility.: DMSO, Ethanol, Methanol
• Water Solubility.: insoluble
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 265.13140809
• Heavy Atom Count: 19
• Complexity: 316

Purity/Quality:

95%,98%, ^*data from raw suppliers

Boc-D-Phe ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=CC=C1)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CC1=CC=CC=C1)C(=O)O
• Description: 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.
• Uses: 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. 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.

Technology Process of Boc-D-phenylalanine

There total 49 articles about Boc-D-phenylalanine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

di-tert-butyl dicarbonate (24424-99-5) + D-(R)-phenylalanine (673-06-3,25191-15-5,658-69-5,67675-33-6) → Boc-D-Phe-OH (18942-49-9)

Guidance literature:

With sodium hydroxide; In water; for 6h;

DOI:10.1021/acs.jmedchem.0c01935

Reference yield: 97.0%

{(R)-1-[((1S,2S)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-methyl-carbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester (185509-03-9) → N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + Boc-D-Phe-OH (18942-49-9)

Guidance literature:

With tetra(n-butyl)ammonium hydroxide; In water; tert-butyl alcohol; for 2.5h; Yields of byproduct given. Title compound not separated from byproducts; Heating;

DOI:10.1021/ja9624073

Reference yield: 33.0%

glycine ethyl ester hydrochloride (5680-79-5,883886-67-7) + 2-tert-Butoxycarbonylamino-3-phenyl-propionic acid (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl ester (74293-09-7) → N-(tert-butoxycarbonyl)-L-phenylalanine (4530-18-1,13734-34-4,18942-49-9) + (2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-acetic acid methyl ester (7625-57-2,26582-93-4,106572-02-5)

Guidance literature:

With 4-methyl-morpholine; In N,N-dimethyl-formamide; at 38 ℃; for 96h;

DOI:10.1016/S0008-6215(00)81893-5

upstream raw materials:

D-(R)-phenylalanine

S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine

N-tert-butoxycarbonyl-D-Phenylalaninol

N-tert-butoxycarbonyl D-phenylalanine p-nitrophenyl ester

Downstream raw materials:

(S)-benzyl 1-((R)-2-(tert-butoxycarbonylamino)-3-phenylpropanoyl)pyrrolidine-2-carboxylate

(R)-tert-butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

[(R)-1-Benzyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

2-(S)-(2-(R)-tert-butoxycarbonylamino-3-phenyl-propionylamino)-5-nitroguanidino-pentanoic acid methyl ester

Refernces

• 1、 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.. "Synthesis and Biological Evaluation of PSMA Ligands with Aromatic Residues and Fluorescent Conjugates Based on Them". supporting information. p. 4532 - 4552. Retrieved 2021/05/06.
• 2、 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. "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". supporting information. p. 2291 - 2309. Retrieved 2021/03/01.