Delt-I

Base Information

• Chemical Name: Delt-I
• CAS No.: 122752-15-2
• Molecular Formula: C37H52 N8 O10
• Molecular Weight: 768.867
• Wikidata: Q105102652
• Mol file: 122752-15-2.mol

Synonyms:(Ala(2))deltorphin I;(D-Ala(2))-deltorphin-I;DELT-I;deltorphin C;deltorphin I;deltorphin I, Ala(2)-;Tyr-Ala-Phe-Asp-Val-Val-Gly-NH2

Chemical Property of Delt-I

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1242.4°Cat760mmHg
• PKA: 4.19±0.10(Predicted)
• Flash Point: 705.2°C
• PSA: 301.24000
• Density: 1.284g/cm³
• LogP: 2.08280
• Storage Temp.: -15°C
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 21
• Exact Mass: 768.38063989
• Heavy Atom Count: 55
• Complexity: 1350

Purity/Quality:

99% ^*data from raw suppliers

Deltorphin I ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(=O)NC(C(C)C)C(=O)NCC(=O)N)NC(=O)C(CC(=O)O)NC(=O)C(CC1=CC=CC=C1)NC(=O)C(C)NC(=O)C(CC2=CC=C(C=C2)O)N
• Isomeric SMILES: C[C@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC(=O)O)C(=O)NC(C(C)C)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N)NC(=O)[C@H](CC2=CC=C(C=C2)O)N
• Uses: Selective delta-opioid receptor agonist

Technology Process of Delt-I

There total 16 articles about Delt-I 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: 71.0%

Z-Tyr(BZl)-D-Ala-Phe-Asp(Bzl)-Val-Val-Gly-NH2 → deltorphin C (122752-15-2)

Guidance literature:

With formic acid; palladium; for 3h; Ambient temperature;

Reference yield:

2,5-dioxopyrrolidin-1-yl (2S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate (3496-11-5) → deltorphin C (122752-15-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 82 percent / N,N-diisopropylethylamine DIEA, HOBt / dimethylformamide / 0 - 20 °C

2: H₂ / 5percent Pd/C / acetic acid; propan-2-ol / 760 Torr / Ambient temperature

3: 75 percent / N-methylmorpholine hydrochloride / dimethylformamide / 4 h / -10 - 0 °C / '

4: H₂ / 5percent Pd/C / acetic acid; propan-2-ol / 760 Torr / Ambient temperature

5: N-methylmorpholine NMM, N,N'-dicyclohexylcarbodiimide DCC, HOBt / dimethylformamide / 1.) 0 deg C, 2 h, 2.) RT, 24 h

6: trifluoroacetic acid TFA / CH₂Cl₂ / 1 h / 0 °C

With 4-methyl-morpholine; hydrogen; N-methylmorpholine hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In dichloromethane; acetic acid; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1016/0223-5234(92)90113-F

Reference yield:

(S)-3-((S)-2-{(R)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-propionylamino}-3-phenyl-propionylamino)-N-{(S)-1-[(S)-1-(carbamoylmethyl-carbamoyl)-2-methyl-propylcarbamoyl]-2-methyl-propyl}-succinamic acid tert-butyl ester (1025941-24-5) → deltorphin C (122752-15-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/0223-5234(92)90113-F

upstream raw materials:

(S)-3-((S)-2-{(R)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-propionylamino}-3-phenyl-propionylamino)-N-{(S)-1-[(S)-1-(carbamoylmethyl-carbamoyl)-2-methyl-propylcarbamoyl]-2-methyl-propyl}-succinamic acid tert-butyl ester

Boc-(R)-Ala

BOC-L-aspartic acid 4-benzyl ester

N-tert-butoxycarbonyl-L-phenylalanine

Refernces

• 1、 Qian,Shenderovich,Kover,Davis,Horvath,Zalewska,Yamamura,Porreca,Hruby. "Probing the stereochemical requirements for receptor recognition of δ opioid agonists through topographic modifications in position 1". . p. 7280 - 7290. Retrieved 1996.
• 2、 Lazarus, LH,Salvadori, S,Grieco, P,Wilson, WE,Tomatis, R. "Unique sequence in deltorphin C confers structural requirement for δ opioid receptor selectivity". . p. 791 - 797. Retrieved 2007/10/02.