Benzyloxycarbonyl-Val-Ala-Asp(OMe)-fluoromethylketone

Base Information

• Chemical Name: Benzyloxycarbonyl-Val-Ala-Asp(OMe)-fluoromethylketone
• CAS No.: 187389-52-2
• Molecular Formula: C₂₂H₃₀FN₃O₇
• Molecular Weight: 467.495
• Hs Code.: 29145090
• DSSTox Substance ID: DTXSID40420586
• Nikkaji Number: J816.404E
• Wikidata: Q72502241
• ChEMBL ID: CHEMBL1213366
• Mol file: 187389-52-2.mol

Synonyms:butyloxycarbonyl-Val-Ala-Asp(OMe)-fluoromethylketone;butyloxycarbonyl-valyl-alanyl-aspartyl-O-methyl-fluoromethyl ketone;z-VAD(OMe)-fmk;z-Val-Ala-Asp(Ome)-fluoromethylketone;z-Val-Ala-Asp(Ome)-FMK;zVAD(OMe) peptide

Chemical Property of Benzyloxycarbonyl-Val-Ala-Asp(OMe)-fluoromethylketone

Chemical Property:

• Vapor Pressure: 2.62E-21mmHg at 25°C
• Melting Point: >190°C (dec.)
• Boiling Point: 732.4°Cat760mmHg
• PKA: 11.05±0.46(Predicted)
• Flash Point: 396.7°C
• PSA: 139.90000
• Density: 1.214g/cm³
• LogP: 2.20130
• Storage Temp.: −20°C
• Solubility.: DMSO: 20 mg/mL
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 14
• Exact Mass: 467.20677847
• Heavy Atom Count: 33
• Complexity: 696

Purity/Quality:

99% ^*data from raw suppliers

Z-VAD-FMK ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(=O)NC(C)C(=O)NC(CC(=O)OC)C(=O)CF)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: C[C@@H](C(=O)N[C@@H](CC(=O)OC)C(=O)CF)NC(=O)[C@H](C(C)C)NC(=O)OCC1=CC=CC=C1
• Description: Z-VAD-FMK (187389-52-2), cell-permeable, methyl ester form. Potent, irreversible pan-caspase inhibitor. Inhibits caspase activity and apoptosis induction in a variety of cell types (IC50 = 1.5 μM). Active in vivo.
• Uses: Z-VAD(OMe)-FMK is a cell-permeable, competitive, and irreversible inhibitor of all caspases. Through this action, it inhibits cleavage of poly(ADP-ribose) polymerase, preventing apoptosis when used at 10-50 μM. It also blocks caspase-mediated apoptosis in vivo. Z-VAD(OMe)-FMK effectively prevents caspase action in inflammasomes.[Cayman Chemical] Z-VAD-FMK is a caspase inhibitor that inhibits apoptosis and caspase processing in Jurkat T cells treated with low concentrations of z-FA-CMK.

Technology Process of Benzyloxycarbonyl-Val-Ala-Asp(OMe)-fluoromethylketone

There total 7 articles about Benzyloxycarbonyl-Val-Ala-Asp(OMe)-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:

(S)-N-(benzyloxycarbonyl)valine (1149-26-4) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3,136132-75-7) + 4-[(S)-11-(9H-fluoren-9-yl)-6-(fluoromethyl)-7-(2-methoxy-2-oxoethyl)-3,9-dioxo-10-oxa-2,4,5,8-tetraazaundec-5-en-1-yl]cyclohexane-1-carboxylic acid → (S)-3-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-propionylamino]-5-fluoro-4-oxo-pentanoic acid methyl ester (634911-81-2,187389-52-2,211918-97-7)

Guidance literature:

4-[(S)-11-(9H-fluoren-9-yl)-6-(fluoromethyl)-7-(2-methoxy-2-oxoethyl)-3,9-dioxo-10-oxa-2,4,5,8-tetraazaundec-5-en-1-yl]cyclohexane-1-carboxylic acid; With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

With piperidine; In N,N-dimethyl-formamide; for 0.166667h;

(S)-N-(benzyloxycarbonyl)valine; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; Further stages;

DOI:10.1039/d1ra03046a

Reference yield:

tert-butyl (S)-3-{[(9H-fluoren-9-yl)methoxycarbonyl]amino}-5-bromo-4-oxopentanoate (294860-44-9) → (S)-3-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-propionylamino]-5-fluoro-4-oxo-pentanoic acid methyl ester (634911-81-2,187389-52-2,211918-97-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: toluene-4-sulfonic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / Inert atmosphere; Reflux

2.1: trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C

3.1: chloro-trimethyl-silane / 20 °C

4.1: sodium acetate / water; ethanol / 3 h / Inert atmosphere; Reflux

5.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C

5.2: 0.17 h

With chloro-trimethyl-silane; tetrabutyl ammonium fluoride; sodium acetate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1039/d1ra03046a

Reference yield:

methyl (S)-3-{[(9H-fluoren-9-yl)methoxycarbonyl]amino}-5-bromo-4-oxopentanoate → (S)-3-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-propionylamino]-5-fluoro-4-oxo-pentanoic acid methyl ester (634911-81-2,187389-52-2,211918-97-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: toluene-4-sulfonic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / Inert atmosphere; Reflux

2.1: sodium acetate / water; ethanol / 3 h / Inert atmosphere; Reflux

3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C

3.2: 0.17 h

With tetrabutyl ammonium fluoride; sodium acetate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1039/d1ra03046a

upstream raw materials:

(S)-N-(benzyloxycarbonyl)valine

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine

tert-butyl (S)-3-{[(9H-fluoren-9-yl)methoxycarbonyl]amino}-5-bromo-4-oxopentanoate

Refernces