benzyloxycarbonyl-Val-Ala-DL-Asp-fluoromethylketone

Base Information

• Chemical Name: benzyloxycarbonyl-Val-Ala-DL-Asp-fluoromethylketone
• CAS No.: 220644-02-0
• Molecular Formula: C21H28 F N3 O7
• Molecular Weight: 453.4613
• Hs Code.: 3504009000
• DSSTox Substance ID: DTXSID60420583
• Nikkaji Number: J709.338A
• Mol file: 220644-02-0.mol

Synonyms:220644-02-0;benzyloxycarbonyl-Val-Ala-DL-Asp-fluoromethylketone;5-fluoro-3-[[(2S)-2-[[(2S)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]propanoyl]amino]-4-oxopentanoic acid;Z-Val-Ala-DL-Asp-fluoromethyl ketone;Z-VA-DL-D-FMK;AC1NUZLU;Z-VA-DL-D(OH)-FMK;carbobenzyloxy-Val-Ala-Asp-alpha-fluoromethylketone;SCHEMBL24213871;DTXSID60420583;z-Val-Ala-DL-Asp fluoromethylketone;MFCD06795862;L-alaninamide, N-[(phenylmethoxy)carbonyl]-L-valyl-N-[1-(carboxymethyl)-3-fluoro-2-oxopropyl]-;benzyloxycarbonyl-Val-Ala-DL-Asp fluoromethyl ketone;benzyloxycarbonyl-Val-Ala-DL-Asp-fluoromethyl ketone;3-[[N-[N-[(Benzyloxy)carbonyl]-L-valyl]-L-alanyl]amino]-4-oxo-5-fluorovaleric acid;L-Alaninamide, N-[(phenylmethoxy)carbonyl]-L-valyl-N-[1-(carboxymethyl)-3-fluoro-2-oxopropyl]- (9CI)

Chemical Property of benzyloxycarbonyl-Val-Ala-DL-Asp-fluoromethylketone

Chemical Property:

• Vapor Pressure: 3.78E-24mmHg at 25°C
• Boiling Point: 758°C at 760 mmHg
• Flash Point: 412.2°C
• PSA: 150.90000
• Density: 1.26g/cm³
• LogP: 2.11290
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 13
• Exact Mass: 453.19112840
• Heavy Atom Count: 32
• Complexity: 680

Purity/Quality:

99%+, ^*data from raw suppliers

Z-Val-Ala-DL-Asp-fluoromethylketone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(=O)NC(C)C(=O)NC(CC(=O)O)C(=O)CF)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: C[C@@H](C(=O)NC(CC(=O)O)C(=O)CF)NC(=O)[C@H](C(C)C)NC(=O)OCC1=CC=CC=C1

Technology Process of benzyloxycarbonyl-Val-Ala-DL-Asp-fluoromethylketone

There total 3 articles about benzyloxycarbonyl-Val-Ala-DL-Asp-fluoromethylketone 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: 91.0%

3-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-propionylamino]-5-fluoro-4-oxo-pentanoic acid tert-butyl ester → benzyloxycarbonyl-Val-Ala-DL-Asp-fluoromethylketone (220644-02-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1016/0040-4039(94)88361-0

Reference yield:

t-butyl 5-fluoro-4-hydroxy-3-nitropentanoate (161401-78-1) → benzyloxycarbonyl-Val-Ala-DL-Asp-fluoromethylketone (220644-02-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / hydrogen / Raney-Nickel / methanol / 12 h / Ambient temperature

2: 97 percent / EDCl, HOBT, DMAP / tetrahydrofuran / 12 h

3: 62 percent / Dess-Martin reagent / CH₂Cl₂ / 0.5 h

4: 91 percent / TFA / CH₂Cl₂ / 0.5 h / Ambient temperature

With dmap; hydrogen; benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; nickel; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/0040-4039(94)88361-0

Reference yield:

3-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-propionylamino]-5-fluoro-4-hydroxy-pentanoic acid tert-butyl ester (161401-80-5) → benzyloxycarbonyl-Val-Ala-DL-Asp-fluoromethylketone (220644-02-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 62 percent / Dess-Martin reagent / CH₂Cl₂ / 0.5 h

2: 91 percent / TFA / CH₂Cl₂ / 0.5 h / Ambient temperature

With Dess-Martin periodane; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/0040-4039(94)88361-0

upstream raw materials:

t-butyl 5-fluoro-4-hydroxy-3-nitropentanoate

3-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-propionylamino]-5-fluoro-4-hydroxy-pentanoic acid tert-butyl ester

Refernces