Boc-D-Pentafluorophenylalanine

Base Information

• Chemical Name: Boc-D-Pentafluorophenylalanine
• CAS No.: 136207-26-6
• Molecular Formula: C₁₄H₁₄F₅NO₄
• Molecular Weight: 355.261
• Hs Code.: 2924297099
• European Community (EC) Number: 671-837-2
• DSSTox Substance ID: DTXSID90929296
• Nikkaji Number: J2.254.342C
• Wikidata: Q72450246
• Mol file: 136207-26-6.mol

Synonyms:136207-26-6;Boc-D-Pentafluorophenylalanine;(R)-2-((tert-Butoxycarbonyl)amino)-3-(perfluorophenyl)propanoic acid;(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(2,3,4,5,6-pentafluorophenyl)propanoic acid;BOC-3-(PENTAFLUOROPHENYL)-D-ALANINE;Boc-DPhe(F5)-OH;DTXSID90929296;UZDKQMIDSLETST-ZCFIWIBFSA-N;MFCD00151892;AKOS024464796;AC-5838;FS-5258;Boc-L-2,3,4,5,6-Pentafluorophenylalanine;A50137;A807040;Boc-pentafluoro-D-phenylalanine, >=98.0% (HPLC);(R)-2-(BOC-AMINO)-3-(PENTAFLUOROPHENYL)PROPIONIC ACID;N-tert-butoxycarbonyl-2,3,4,5,6-pentafluoro-D-phenylalanine;(R)-2-((tert-Butoxycarbonyl)amino)-3-(perfluorophenyl)propanoicacid;(r)-2-(tert-butoxycarbonylamino)-3-(perfluorophenyl)propanoic acid;(2R)-2-(tert-Butoxycarbonylamino)-3-(pentafluorophenyl)propionic acid;N-[tert-Butoxy(hydroxy)methylidene]-2,3,4,5,6-pentafluorophenylalanine;N-alpha-t-Butyloxycarbonyl-D-pentafluorophenylalanine (Boc-D-Phe(F5)-OH)

Chemical Property of Boc-D-Pentafluorophenylalanine

Chemical Property:

• Vapor Pressure: 1.7E-07mmHg at 25°C
• Refractive Index: 1.476
• Boiling Point: 411.1 °C at 760 mmHg
• PKA: 3.70±0.20(Predicted)
• Flash Point: 202.4 °C
• PSA: 75.63000
• Density: 1.422 g/cm³
• LogP: 3.29340
• Storage Temp.: -15°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 355.08429874
• Heavy Atom Count: 24
• Complexity: 457

Purity/Quality:

97% ^*data from raw suppliers

Boc-pentafluoro-D-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=C(C(=C(C(=C1F)F)F)F)F)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CC1=C(C(=C(C(=C1F)F)F)F)F)C(=O)O
• Uses: BOC-D-Pentafluorophenylalanine, is a Phenylalanine derivative, used in peptide chemistry.

Technology Process of Boc-D-Pentafluorophenylalanine

There total 1 articles about Boc-D-Pentafluorophenylalanine 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: 95.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-tert-butyl 2-amino-3-(perfluorophenyl)propanoate → (S)-2-((tert-butoxycarbonyl)amino)-3-(perfluorophenyl)propanoic acid (136207-26-6,34702-60-8)

Guidance literature:

(S)-tert-butyl 2-amino-3-(perfluorophenyl)propanoate; With trifluoroacetic acid; for 0.5h; Inert atmosphere;

di-tert-butyl dicarbonate; With sodium carbonate; In 1,4-dioxane; water; at 0 - 20 ℃; for 12h; Inert atmosphere;

DOI:10.1021/jm9015685

Reference yield: 72.0%

N-hydroxyphthalimide (524-38-9) + (S)-2-((tert-butoxycarbonyl)amino)-3-(perfluorophenyl)propanoic acid (136207-26-6,34702-60-8) → 1,3-dioxoisoindolin-2-yl 2-((tert-butoxycarbonyl)amino)-3-(perfluorophenyl)propanoate

Guidance literature:

N-hydroxyphthalimide; (S)-2-((tert-butoxycarbonyl)amino)-3-(perfluorophenyl)propanoic acid; With dmap; In dichloromethane; for 0.0833333h; Inert atmosphere;

With diisopropyl-carbodiimide; In dichloromethane; at 25 ℃; for 12h; Sealed tube; Inert atmosphere;

DOI:10.1002/anie.202112454

Reference yield: 63.0%

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride (7524-50-7) + (S)-2-((tert-butoxycarbonyl)amino)-3-(perfluorophenyl)propanoic acid (136207-26-6,34702-60-8) → (S)-methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-(perfluorophenyl)propanamido)-3-phenylpropanoate (1207604-45-2)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 34 ℃; for 24h; Cooling with ice;

DOI:10.1021/jacs.1c01951

upstream raw materials:

di-tert-butyl dicarbonate

Downstream raw materials:

C₁₈H₁₇F₅N₂O₆

2',3',4',5',6'-Pentafluoro-L-phenylalanine

(S)-2-Amino-3-pentafluorophenyl-propionic acid methyl ester

(S)-methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-(perfluorophenyl)propanamido)-3-(perfluorophenyl)propanoate

Refernces