Dolastatin 10

Base Information

• Chemical Name: Dolastatin 10
• CAS No.: 110417-88-4
• Molecular Formula: C42H68 N6 O6 S
• Molecular Weight: 785.105
• UNII: EI946JT51X
• DSSTox Substance ID: DTXSID70911674
• Nikkaji Number: J359.711C
• Wikidata: Q27104943
• NCI Thesaurus Code: C1300
• Metabolomics Workbench ID: 133452
• ChEMBL ID: CHEMBL39541
• Mol file: 110417-88-4.mol

Synonyms:Deo-Dola 10;deo-dolastatin 10;dolastatin 10;isodolastatin 10;NSC 376128

Chemical Property of Dolastatin 10

Chemical Property:

• Vapor Pressure: 1.95E-33mmHg at 25°C
• Boiling Point: 903.6°Cat760mmHg
• PKA: 13.81±0.46(Predicted)
• Flash Point: 500.3°C
• PSA: 161.65000
• Density: 1.116g/cm³
• LogP: 5.91010
• Solubility.: ≥78.5 mg/mL in EtOH; insoluble in H2O; ≥67.2 mg/mL in DMSO
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 21
• Exact Mass: 784.49210508
• Heavy Atom Count: 55
• Complexity: 1220

Purity/Quality:

98%min ^*data from raw suppliers

Dolastatin10 ^*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)NC(CC2=CC=CC=C2)C3=NC=CS3)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)N[C@@H](CC2=CC=CC=C2)C3=NC=CS3)OC)OC)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)N(C)C
• Recent ClinicalTrials: Dolastatin 10 in Treating Patients With Metastatic Pancreatic Cancer

Technology Process of Dolastatin 10

There total 91 articles about Dolastatin 10 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: 97.0%

Dov-Val-Dil trifluoroacetate + (2R,3R)-3-methoxy-2-methyl-N-[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]-3-[(2S)-pyrrolidin-2-yl]propanamide, trifluoroacetic acid salt → dolastatin 10 (110417-88-4)

Guidance literature:

With triethylamine; diethyl dicarbonate; In 1,2-dimethoxyethane; 1.) 0 deg C, 1 h, 2.) r.t., 2 h;

DOI:10.1039/P19960000859

Reference yield: 90.0%

N,N-dimethyl-L-valine (2812-32-0) + (2S)-2-amino-N-[(3R,5S)-3-methoxy-1-[(2S)-2-[(1R,2R)-1-methoxy-2-methyl-2-[[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]carbamoyl]ethyl]pyrrolidin-1-yl]-5-methyl-1-oxoheptan-4-yl]-N,3-dimethylbutanamide → dolastatin 10 (110417-88-4)

Guidance literature:

With 4-methyl-morpholine; diethyl dicarbonate; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)92123-3

Reference yield:

Boc-L-Pro-H (69610-41-9,117625-90-8) → dolastatin 10 (110417-88-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 18 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

2: 41 percent / BF₃*OEt₂ / CH₂Cl₂

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

4: benzotriazolyloxytris(dimethylamino)phosphonium hexafluorophosphate, iso-Pr₂NEt / acetonitrile

5: HCl / dioxane / 1 h / Ambient temperature

6: diethyl phosphorocyanidate, Et₃N / dimethylformamide

With hydrogenchloride; diethyl cyanophosphonate; boron trifluoride diethyl etherate; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

DOI:10.1248/cpb.43.1706

upstream raw materials:

N,N-dimethyl-L-valine

tert-butyl (2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-{[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino}propyl]pyrrolidine-1-carboxylate

(3R,4S,5S)-tert-butyl 4-((S)-2-((S)-2-(dimethylamino)-3-methylbutanamido)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoate

(3R,4S,5S)-4-((S)-2-((S)-2-(dimethylamino)-3-methylbutanamido)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoic acid

Refernces

• 1、 Hamada, Yasumasa,Hayashi, Kyoko,Shioiri, Takayuki. "Efficient stereoselective synthesis of dolastatin 10, an antineoplastic peptide from a sea hare". . p. 931 - 934. Retrieved 1991.
• 2、 Mordant, Céline,Reymond, Sébastien,Tone, Hitoshi,Lavergne, Damien,Touati, Ridha,Ben Hassine, Bechir,Ratovelomanana-Vidal, Virginie,Genet, Jean-Pierre. "Total synthesis of dolastatin 10 through ruthenium-catalyzed asymmetric hydrogenations". . p. 6115 - 6123. Retrieved 2008/02/04.