Z-DAP(FMOC)-OH

Base Information

• Chemical Name: Z-DAP(FMOC)-OH
• CAS No.: 142855-80-9
• Molecular Formula: C26H24N2O6
• Molecular Weight: 460.486
• Hs Code.: 29242990
• Nikkaji Number: J636.505A
• Mol file: 142855-80-9.mol

Synonyms:Z-L-Dap(Fmoc)-OH;

Chemical Property of Z-DAP(FMOC)-OH

Chemical Property:

• Vapor Pressure: 6.13E-22mmHg at 25°C
• Refractive Index: 1.623
• Boiling Point: 722.985 °C at 760 mmHg
• Flash Point: 391.048 °C
• PSA: 96.89000
• Density: 1.32 g/cm³
• LogP: 4.52400
• Storage Temp.: Store at 0°C
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 460.16343649
• Heavy Atom Count: 34
• Complexity: 687

Purity/Quality:

99.3% ^*data from raw suppliers

N-alpha-Z-Nbeta-Fmoc-L-2,3-diaminopropionic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NC(CNC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)C(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)N[C@@H](CNC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)C(=O)O
• Uses: N-Benzyloxycarbonyl-3-(Fmoc-amino)-L-alanine is a useful intermediate for organic synthesis.

Technology Process of Z-DAP(FMOC)-OH

There total 3 articles about Z-DAP(FMOC)-OH 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%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + (S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoic acid (35761-26-3) → Nα-Cbz-Nβ-Fmoc-Apa (142855-80-9)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃; for 3h;

DOI:10.1016/S0968-0896(01)00228-0

Reference yield:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoic acid (35761-26-3) → Nα-Cbz-Nβ-Fmoc-Apa (142855-80-9)

Guidance literature:

With sodium hydrogencarbonate; In water; acetone; for 3h; Yield given;

DOI:10.1016/0040-4039(93)88067-S

Reference yield:

N-benzyloxycarbonyl-L-asparagine (2304-96-3) → Nα-Cbz-Nβ-Fmoc-Apa (142855-80-9)

Guidance literature:

Multi-step reaction with 2 steps

1: C₆H₅I(CF₃COO)2, pyridine / H₂O; dimethylformamide / 4.5 h / Ambient temperature

2: NaHCO₃ / H₂O; acetone / 3 h

With pyridine; sodium hydrogencarbonate; bis-[(trifluoroacetoxy)iodo]benzene; In water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/0040-4039(93)88067-S

upstream raw materials:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoic acid

(fluorenylmethoxy)carbonyl chloride

N-benzyloxycarbonyl-L-asparagine

Downstream raw materials:

Cbz-N^β-(bis-Bu^t-acetate)-Apa-OTmse

(S)-3-Amino-2-benzyloxycarbonylamino-propionic acid 2-trimethylsilanyl-ethyl ester

N^α-Cbz-N^β-Fmoc-Apa-OTmse

[2-benzyloxycarbonylamino-3-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-acetic acid tert-butyl ester

Refernces

• 1、 Marrano,de Macedo,Gagnon,Lapierre,Gravel,Keillor. "Synthesis and evaluation of novel dipeptide-bound 1,2,4-thiadiazoles as irreversible inhibitors of guinea pig liver transglutaminase.". . p. 3231 - 3241. Retrieved 2007/10/03.