L-Leucine, L-phenylalanylglycylglycyl-L-phenylalanyl-

Base Information

• Chemical Name: L-Leucine, L-phenylalanylglycylglycyl-L-phenylalanyl-
• CAS No.: 60254-86-6
• Molecular Formula: C₂₈H₃₇N₅O₆
• Molecular Weight: 539.632
• DSSTox Substance ID: DTXSID40477257
• Nikkaji Number: J862.003B
• Wikidata: Q82309629
• Mol file: 60254-86-6.mol

Synonyms:L-Leucine, L-phenylalanylglycylglycyl-L-phenylalanyl-;60254-86-6;DTXSID40477257

Chemical Property of L-Leucine, L-phenylalanylglycylglycyl-L-phenylalanyl-

Chemical Property:

• XLogP3: -0.4
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 15
• Exact Mass: 539.27438392
• Heavy Atom Count: 39
• Complexity: 823

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(C(=O)O)NC(=O)C(CC1=CC=CC=C1)NC(=O)CNC(=O)CNC(=O)C(CC2=CC=CC=C2)N
• Isomeric SMILES: CC(C)C[C@@H](C(=O)O)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CNC(=O)CNC(=O)[C@H](CC2=CC=CC=C2)N

Technology Process of L-Leucine, L-phenylalanylglycylglycyl-L-phenylalanyl-

There total 13 articles about L-Leucine, L-phenylalanylglycylglycyl-L-phenylalanyl- 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:

L-phenylalanyl-L-leucine benzyl ester (63649-15-0) → Tyr-Gly-Gly-Phe-Leu (60254-86-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 69 percent / N-methylmorpholine, isobutyl chloroformate / tetrahydrofuran; dimethylformamide / 5 h / Ambient temperature

2: trifluoroacetic acid (TFA) / 1 h / 0 °C

3: 2.) 2-diethylaminoethylamine (DEAEA) / 1) DMF, RT, 21h, 2) 6h

4: trifluoroacetic acid (TFA) / 1 h / 0 °C

5: 50 percent / Et₃N, N-hydroxysuccinimide, DCC / dimethylformamide / Ambient temperature

6: 1.) H₂, 2.) 2M HCl / 1.) 5percent Pd/C / 1.) 80percent AcOH, 5 h, 2.) dioxane, RT, 1h

With 4-methyl-morpholine; hydrogenchloride; 1-hydroxy-pyrrolidine-2,5-dione; hydrogen; triethylamine; N,N-diethylethylenediamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; isobutyl chloroformate; palladium on activated charcoal; In tetrahydrofuran; N,N-dimethyl-formamide;

Reference yield:

N-(tert-butoxycarbonyl)-L-phenylalanine benzyl ester (66617-58-1) → Tyr-Gly-Gly-Phe-Leu (60254-86-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 100 percent / DMAP / acetonitrile / Ambient temperature

2: H₂ / 5percent (w/w) Pd/C / methanol / 2 h

3: 72 percent / DCC / ethyl acetate / Ambient temperature

4: 76 percent / dimethylformamide / 48 h / Ambient temperature

5: 100 percent / trifluoroacetic acid (TFA) / 1 h / 0 °C

6: 69 percent / N-methylmorpholine, isobutyl chloroformate / tetrahydrofuran; dimethylformamide / 5 h / Ambient temperature

7: trifluoroacetic acid (TFA) / 1 h / 0 °C

8: 2.) 2-diethylaminoethylamine (DEAEA) / 1) DMF, RT, 21h, 2) 6h

9: trifluoroacetic acid (TFA) / 1 h / 0 °C

10: 50 percent / Et₃N, N-hydroxysuccinimide, DCC / dimethylformamide / Ambient temperature

11: 1.) H₂, 2.) 2M HCl / 1.) 5percent Pd/C / 1.) 80percent AcOH, 5 h, 2.) dioxane, RT, 1h

With 4-methyl-morpholine; hydrogenchloride; dmap; 1-hydroxy-pyrrolidine-2,5-dione; hydrogen; triethylamine; N,N-diethylethylenediamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; isobutyl chloroformate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

(BOC)2Phe-OH (113568-21-1) → Tyr-Gly-Gly-Phe-Leu (60254-86-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 72 percent / DCC / ethyl acetate / Ambient temperature

2: 76 percent / dimethylformamide / 48 h / Ambient temperature

3: 100 percent / trifluoroacetic acid (TFA) / 1 h / 0 °C

4: 69 percent / N-methylmorpholine, isobutyl chloroformate / tetrahydrofuran; dimethylformamide / 5 h / Ambient temperature

5: trifluoroacetic acid (TFA) / 1 h / 0 °C

6: 2.) 2-diethylaminoethylamine (DEAEA) / 1) DMF, RT, 21h, 2) 6h

7: trifluoroacetic acid (TFA) / 1 h / 0 °C

8: 50 percent / Et₃N, N-hydroxysuccinimide, DCC / dimethylformamide / Ambient temperature

9: 1.) H₂, 2.) 2M HCl / 1.) 5percent Pd/C / 1.) 80percent AcOH, 5 h, 2.) dioxane, RT, 1h

With 4-methyl-morpholine; hydrogenchloride; 1-hydroxy-pyrrolidine-2,5-dione; hydrogen; triethylamine; N,N-diethylethylenediamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; isobutyl chloroformate; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide;

upstream raw materials:

H-Gly-Gly-Phe-Leu-OBzl

L-phenylalanyl-L-leucine benzyl ester

N-(tert-butoxycarbonyl)-L-phenylalanine benzyl ester

(S)-benzyl 2-((S)-2-(2-aminoacetamido)-3-phenylpropanamido)-4-methylpentanoate