BOC-L-PENTAFLUOROPHENYLALANINE

Base Information

• Chemical Name: BOC-L-PENTAFLUOROPHENYLALANINE
• CAS No.: 34702-60-8
• Molecular Formula: C₁₄H₁₄F₅NO₄
• Molecular Weight: 355.261
• Hs Code.: 2924299090
• Mol file: 34702-60-8.mol

Synonyms:N-BOC-Pentafluoro-L-phenylalanine;N-tert-Butoxycarbonyl-2,3,4,5,6-pentafluoro-L-phenylalanine;N-(tert-butoxycarbonyl)-2,3,4,5,6-pentafluoro-L-phenylalanine;(2S)-2-({[(2-Methyl-2-propanyl)oxy]carbonyl}amino)-3-(pentafluorophenyl)propanoic acid;2,3,4,5,6-Pentafluoro-N-{[(2-methyl-2-propanyl)oxy]carbonyl}-L-phenylalanine;L-phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-2,3,4,5,6-pentafluoro-;N-(tert-Butoxycarbonyl)-2,3,4,5,6-pentafluoro-L-phenylalanine;

Chemical Property of BOC-L-PENTAFLUOROPHENYLALANINE

Chemical Property:

• 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

Purity/Quality:

98%,99%, ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Uses: BOC-L-Pentafluorophenylalanine is an intermediate used in the self-assembly of tripeptides into functional coating material that resists biofouling.

Technology Process of BOC-L-PENTAFLUOROPHENYLALANINE

There total 2 articles about BOC-L-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:

→ 2-tert-Butoxycarbonylamino-3-pentafluorophenyl-propionic acid (168110-58-5,34702-60-8)

Guidance literature:

Verb.4, Kohlensaeure-mono-t-butylester-azid;

DOI:10.1002/hlca.19710540739

Reference yield:

(S)-2-((tert-butoxycarbonyl)amino)-3-(perfluorophenyl)propanoic acid (136207-26-6,34702-60-8) → Boc-Dmaa-D-Pro-Acpc-Phe(5F)-NMe2

Guidance literature:

Multi-step reaction with 7 steps

1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 21 - 23 °C

2: hydrogenchloride / 1,4-dioxane / 1 h / 21 - 23 °C

3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 21 - 23 °C

4: hydrogenchloride / 1,4-dioxane / 1 h / 21 - 23 °C

5: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 21 - 23 °C

6: hydrogenchloride / 1,4-dioxane / 1 h / 21 - 23 °C

7: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / dichloromethane / 21 - 23 °C

With hydrogenchloride; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; dichloromethane;

DOI:10.1021/jacs.5b07726

upstream raw materials:

di-tert-butyl dicarbonate

Downstream raw materials:

C₁₈H₁₇F₅N₂O₆

Refernces