CID 11016408

Base Information

• Chemical Name: CID 11016408
• CAS No.: 119613-54-6
• Molecular Formula: C₂₄H₃₇N₇O₄
• Molecular Weight: 487.602
• European Community (EC) Number: 686-402-2
• Nikkaji Number: J602.297I
• Wikidata: Q105025015
• Mol file: 119613-54-6.mol

Synonyms:Nephilatoxin 11;119613-54-6;(2S)-N-[5-[[(2S)-2,5-diaminopentanoyl]amino]pentyl]-2-[[2-(1H-indol-3-yl)acetyl]amino]butanediamide

Chemical Property of CID 11016408

Chemical Property:

• PSA: 198.22000
• LogP: 2.81310
• Storage Temp.: -15°C
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 16
• Exact Mass: 487.29070269
• Heavy Atom Count: 35
• Complexity: 705

Purity/Quality:

99%+, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CC(=O)NC(CC(=O)N)C(=O)NCCCCCNC(=O)C(CCCN)N
• Isomeric SMILES: C1=CC=C2C(=C1)C(=CN2)CC(=O)N[C@@H](CC(=O)N)C(=O)NCCCCCNC(=O)[C@H](CCCN)N

Technology Process of CID 11016408

There total 10 articles about CID 11016408 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:

5-hydroxypentylamine (2508-29-4) → NPTX-11 (119613-54-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 99 percent / aq. Na₂CO₃ / 12 h / Ambient temperature

2: 98 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

3: 99 percent / NaN₃ / dimethylformamide / 12 h / Ambient temperature

4: 1) trifluoroacetic acid, 2) triethylamine / 1) CH₂Cl₂, r.t., 3 h, 2) DMF, r.t., 12 h

5: 1) trifluoroacetic acid, 2) triethylamine / 1) CH₂Cl₂, r.t., 3 h, 2) DMF, r.t., 12 h

6: hydrogen / 10percent Pd-C / ethanol / 3.5 h / 760 Torr

7: triethylamine / dimethylformamide / 17 h / Ambient temperature

8: 1) trifluoroacetic acid, 2) hydrogen / 2) 10percent Pd-C / 1) CH₂Cl₂, r.t., 3 h, 2) EtOH, 1 atm, 5 h

With pyridine; sodium azide; hydrogen; sodium carbonate; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)78872-1

Reference yield:

N-(tert-butyloxycarbonyl)-5-aminopentanol (75178-90-4) → NPTX-11 (119613-54-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 98 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

2: 99 percent / NaN₃ / dimethylformamide / 12 h / Ambient temperature

3: 1) trifluoroacetic acid, 2) triethylamine / 1) CH₂Cl₂, r.t., 3 h, 2) DMF, r.t., 12 h

4: 1) trifluoroacetic acid, 2) triethylamine / 1) CH₂Cl₂, r.t., 3 h, 2) DMF, r.t., 12 h

5: hydrogen / 10percent Pd-C / ethanol / 3.5 h / 760 Torr

6: triethylamine / dimethylformamide / 17 h / Ambient temperature

7: 1) trifluoroacetic acid, 2) hydrogen / 2) 10percent Pd-C / 1) CH₂Cl₂, r.t., 3 h, 2) EtOH, 1 atm, 5 h

With pyridine; sodium azide; hydrogen; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)78872-1

Reference yield:

(5-azido-pentyl)carbamic acid tert-butyl ester (129392-86-5) → NPTX-11 (119613-54-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) trifluoroacetic acid, 2) triethylamine / 1) CH₂Cl₂, r.t., 3 h, 2) DMF, r.t., 12 h

2: 1) trifluoroacetic acid, 2) triethylamine / 1) CH₂Cl₂, r.t., 3 h, 2) DMF, r.t., 12 h

3: hydrogen / 10percent Pd-C / ethanol / 3.5 h / 760 Torr

4: triethylamine / dimethylformamide / 17 h / Ambient temperature

5: 1) trifluoroacetic acid, 2) hydrogen / 2) 10percent Pd-C / 1) CH₂Cl₂, r.t., 3 h, 2) EtOH, 1 atm, 5 h

With hydrogen; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)78872-1

upstream raw materials:

((S)-4-tert-Butoxycarbonylamino-4-{5-[(S)-3-carbamoyl-2-(2-1H-indol-3-yl-acetylamino)-propionylamino]-pentylcarbamoyl}-butyl)-carbamic acid benzyl ester

indole-3-acetic acid

Fmoc-Orn(Boc)-OH

N^α-(Fmoc-L-Asp)-N^ε-<1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl>-cadaverine

Refernces

• 1、 Miyashita, Masaaki,Sato, Hideaki,Yoshikoshi, Akira,Toki, Takashi,Matshushita, Masayuki,Irie, Hiroshi,Yanami, Tetsuji,Kikuchi, Yasuo,Takasaki, Chikahisa,Nakajima, Terumi. "Synthetic studies on spider neurotoxins (I): Total synthesis of nephilatoxins (NPTX-9) and NPTX-11, new neurotoxins of Joro spider (Nephila clavata)". . p. 2833 - 2836. Retrieved 2007/10/02.