Soblidotin

Base Information

• Chemical Name: Soblidotin
• CAS No.: 149606-27-9
• Molecular Formula: C39H67 N5 O6
• Molecular Weight: 701.991
• UNII: DQC51A0WQH
• DSSTox Substance ID: DTXSID901031350
• Nikkaji Number: J697.490B
• Wikidata: Q27276538
• NCI Thesaurus Code: C26672
• Metabolomics Workbench ID: 153623
• ChEMBL ID: CHEMBL3989512
• Mol file: 149606-27-9.mol

Synonyms:auristatin PE;N(2)-(N,N-dimethyl-valyl)-N-(2-methoxy-4-(2-(1-methoxy-2-methyl-3-oxo-3-((2-phenylethyl)amino)propyl)-1-pyrrolidinyl)-1-(1-methylpropyl)-4-oxobutyl)-N-methyl-valinamide;soblidotin;TZT 1027;TZT-1027

Chemical Property of Soblidotin

Chemical Property:

• Vapor Pressure: 1.1E-28mmHg at 25°C
• Melting Point: 73-79 °C
• Boiling Point: 843.4°Cat760mmHg
• PKA: 13.95±0.46(Predicted)
• Flash Point: 463.9°C
• PSA: 120.52000
• Density: 1.064g/cm³
• LogP: 4.71230
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 20
• Exact Mass: 701.50913487
• Heavy Atom Count: 50
• Complexity: 1060

Purity/Quality:

99% ^*data from raw suppliers

Soblidotin 99.64% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C(C(CC(=O)N1CCCC1C(C(C)C(=O)NCCC2=CC=CC=C2)OC)OC)N(C)C(=O)C(C(C)C)NC(=O)C(C(C)C)N(C)C
• Isomeric SMILES: CC[C@H](C)[C@@H]([C@@H](CC(=O)N1CCC[C@H]1[C@@H]([C@@H](C)C(=O)NCCC2=CC=CC=C2)OC)OC)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)N(C)C
• Recent ClinicalTrials: Soblidotin and Gemcitabine in Treating Patients With Locally Advanced or Metastatic Solid Tumors
• Recent EU Clinical Trials: A phase II study of intravenous TZT-1027, administered weekly times two, every three weeks, to patients with advanced or metastatic soft tissue sarcomas (STS) with prior exposure to doxorubicin-based chemotherapy

Technology Process of Soblidotin

There total 11 articles about Soblidotin 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:

phenethylamine (64-04-0) + Dov-Val-Dil-Dap (163768-53-4) → TZT-1027 (149606-27-9)

Guidance literature:

With diethyl cyanophosphonate; triethylamine; In N,N-dimethyl-formamide; Yield given;

DOI:10.1248/cpb.43.1706

Reference yield:

3-methoxy-2-methyl-N-phenethyl-3-pyrrolidin-2-yl-propionamide + (3R,4S,5S)-4-((S)-2-((S)-2-(dimethylamino)-3-methylbutanamido)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoic acid (133120-89-5) → TZT-1027 (149606-27-9)

Guidance literature:

With triethylamine; diethyl cyano phosphate; In DMF (N,N-dimethyl-formamide);

Reference yield:

(3R,4S,5S)-4--3-methoxy-5-methylheptanoic acid (135383-56-1) → TZT-1027 (149606-27-9)

Guidance literature:

Multi-step reaction with 9 steps

1: H₂SO₄ / CH₂Cl₂

2: H₂ / 5percent Pd/C / 2-methyl-propan-2-ol; H₂O / 2 h

3: 1,3-dicyclohexylcarbodiimide / CH₂Cl₂

4: H₂ / 5percent Pd/C / 2-methyl-propan-2-ol; H₂O / 2 h

5: diethyl phosphorocyanidate, Et₃N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h

6: trifluoroacetic acid / CH₂Cl₂ / 1 h / Ambient temperature

7: diethyl phosphorocyanidate, Et₃N / dimethylformamide / a) 0 deg C, 2 h, b) RT, 16 h

8: H₂ / 5percent Pd/C / 2-methyl-propan-2-ol; H₂O / 2 h

9: diethyl phosphorocyanidate, Et₃N / dimethylformamide

With diethyl cyanophosphonate; sulfuric acid; hydrogen; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1248/cpb.43.1706

upstream raw materials:

phenethylamine

Dov-Val-Dil-Dap

(3R,4S,5S)-4--3-methoxy-5-methylheptanoic acid

tert-Butyl (3R,4S,5S)-3-methoxy-4--5-methylheptanoate

Refernces

• 1、 Miyazaki,Kobayashi,Natsume,Gondo,Mikami,Sakakibara,Tsukagoshi. "Synthesis and antitumor activity of novel dolastatin 10 analogs". . p. 1706 - 1718. Retrieved 2007/10/03.