1-[(Benzyloxy)carbonyl]-5-oxo-D-prolyl-L-leucyl-L-prolinamide

Base Information

• Chemical Name: 1-[(Benzyloxy)carbonyl]-5-oxo-D-prolyl-L-leucyl-L-prolinamide
• CAS No.: 78664-75-2
• Molecular Formula: C24H32N4O6
• Molecular Weight: 472.541
• DSSTox Substance ID: DTXSID60709385
• Wikidata: Q82644290
• Mol file: 78664-75-2.mol

Synonyms:78664-75-2;Z-D-Glp-Leu-Pro-NH2;SCHEMBL11176046;DTXSID60709385;OJVZEOJUOWAZMR-GBESFXJTSA-N;1-[(Benzyloxy)carbonyl]-5-oxo-D-prolyl-L-leucyl-L-prolinamide

Chemical Property of 1-[(Benzyloxy)carbonyl]-5-oxo-D-prolyl-L-leucyl-L-prolinamide

Chemical Property:

• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 472.23218475
• Heavy Atom Count: 34
• Complexity: 794

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(C(=O)N1CCCC1C(=O)N)NC(=O)C2CCC(=O)N2C(=O)OCC3=CC=CC=C3
• Isomeric SMILES: CC(C)C[C@@H](C(=O)N1CCC[C@H]1C(=O)N)NC(=O)[C@H]2CCC(=O)N2C(=O)OCC3=CC=CC=C3

Technology Process of 1-[(Benzyloxy)carbonyl]-5-oxo-D-prolyl-L-leucyl-L-prolinamide

There total 4 articles about 1-[(Benzyloxy)carbonyl]-5-oxo-D-prolyl-L-leucyl-L-prolinamide 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:

H-Leu-Pro-NH2*HCl (78664-34-3) + Z-D-pGlu-OPfp (78685-16-2) → N-(benzyloxycarbonyl)-D-pyroglutamyl-L-leucyl-L-prolinamide (78664-75-2)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 0 - 5 ℃; for 0.166667h; Yield given;

DOI:10.1021/jm00372a006

Reference yield:

N-[(1,1-dimethylethoxy)carbonyl]-L-leucine pentafluorophenyl ester (50903-50-9) → N-(benzyloxycarbonyl)-D-pyroglutamyl-L-leucyl-L-prolinamide (78664-75-2)

Guidance literature:

Multi-step reaction with 3 steps

1: DMFA / 1 h / Ambient temperature

2: 2 N HCl / ethyl acetate / 1 h / Ambient temperature

3: Et₃N / dimethylformamide / 0.17 h / 0 - 5 °C

With hydrogenchloride; triethylamine; N,N-dimethyl-formamide; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00372a006

Reference yield:

N-(t-butoxycarbonyl)-L-leucyl-L-prolinamide (105443-86-5) → N-(benzyloxycarbonyl)-D-pyroglutamyl-L-leucyl-L-prolinamide (78664-75-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 2 N HCl / ethyl acetate / 1 h / Ambient temperature

2: Et₃N / dimethylformamide / 0.17 h / 0 - 5 °C

With hydrogenchloride; triethylamine; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00372a006

upstream raw materials:

H-Leu-Pro-NH₂*HCl

Z-D-pGlu-OPfp

N-[(1,1-dimethylethoxy)carbonyl]-L-leucine pentafluorophenyl ester

N-(t-butoxycarbonyl)-L-leucyl-L-prolinamide