Dmt-Pro-Phe-Phe-NH2

Base Information

• Chemical Name: Dmt-Pro-Phe-Phe-NH2
• CAS No.: 596792-36-8
• Molecular Formula: C34H41N5O5
• Molecular Weight: 599.73
• DSSTox Substance ID: DTXSID10435187
• Nikkaji Number: J1.913.647G
• Wikidata: Q82249934
• ChEMBL ID: CHEMBL331325
• Mol file: 596792-36-8.mol

Synonyms:Dmt-Pro-Phe-Phe-NH2;CHEMBL331325;Dmt-endomorphin-2;596792-36-8;D05EZE;DTXSID10435187;BDBM50149384;(2S)-1-[(2S)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)propanoyl]-N-[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]pyrrolidine-2-carboxamide;(S)-1-[(S)-2-Amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionyl]-pyrrolidine-2-carboxylic acid [(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-phenyl-ethyl]-amide

Chemical Property of Dmt-Pro-Phe-Phe-NH2

Chemical Property:

• XLogP3: 3.3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 12
• Exact Mass: 599.31076943
• Heavy Atom Count: 44
• Complexity: 969

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1CC(C(=O)N2CCCC2C(=O)NC(CC3=CC=CC=C3)C(=O)NC(CC4=CC=CC=C4)C(=O)N)N)C)O
• Isomeric SMILES: CC1=CC(=CC(=C1C[C@@H](C(=O)N2CCC[C@H]2C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)N[C@@H](CC4=CC=CC=C4)C(=O)N)N)C)O

Technology Process of Dmt-Pro-Phe-Phe-NH2

There total 12 articles about Dmt-Pro-Phe-Phe-NH2 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: 89.1%

[(S)-2-{(S)-2-[(S)-1-((S)-1-Carbamoyl-2-phenyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-pyrrolidin-1-yl}-1-(4-hydroxy-2,6-dimethyl-benzyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester (579491-05-7) → H-Tyr(2,6-Me2)-Pro-Phe-Phe-NH2 (596792-36-8)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 1h;

DOI:10.1016/S0968-0896(03)00068-3

Reference yield: 47.0%

Fmoc-Pro-OH (71989-31-6) + N-Fmoc L-Phe (35661-40-6) → H-Tyr(2,6-Me2)-Pro-Phe-Phe-NH2 (596792-36-8)

Guidance literature:

N-Fmoc L-Phe; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 0.666667h;

With 4-methylpiperidin; In N,N-dimethyl-formamide; for 0.333333h;

Fmoc-Pro-OH; N-Fmoc L-Phe; Boc-Dmt(*)-OH; Further stages;

DOI:10.1021/acs.jmedchem.8b01282

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → H-Tyr(2,6-Me2)-Pro-Phe-Phe-NH2 (596792-36-8)

Guidance literature:

Multi-step reaction with 7 steps

1: N-methylmorpholine

2: 70.5 percent / Et₃N / tetrahydrofuran; dimethylformamide / 0 - 4 °C

3: HCl / dioxane

4: 78 percent / N-methylmorpholine / tetrahydrofuran; dimethylformamide / 0 - 4 °C

5: HCl / dioxane

6: 61 percent / benzotriazol-1-yloxytripyrrolidinophosphonium PF₆^(1-); N,N-diisopropylethylamine / dimethylformamide / 4 °C

7: 89.1 percent / HCl / dioxane / 1 h / 20 °C

With 4-methyl-morpholine; hydrogenchloride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(03)00068-3

upstream raw materials:

[(S)-2-{(S)-2-[(S)-1-((S)-1-Carbamoyl-2-phenyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-pyrrolidin-1-yl}-1-(4-hydroxy-2,6-dimethyl-benzyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

N-tert-butoxycarbonyl-L-phenylalanine

(S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropionamide

Boc-Phe-O-COO-isoBu

Downstream raw materials:

H-Tyr(2,6-Me₂-3,5-I₂)-Pro-Phe-Phe-NH₂