epothilone F

Base Information

• Chemical Name: epothilone F
• CAS No.: 208518-52-9
• Molecular Formula: C27H41NO7S
• Molecular Weight: 523.68
• UNII: GFX93BX7K3
• Nikkaji Number: J1.198.784B,J1.475.276E
• Wikidata: Q77569085
• Metabolomics Workbench ID: 103212
• ChEMBL ID: CHEMBL513726
• Mol file: 208518-52-9.mol

Synonyms:epothilone F

Chemical Property of epothilone F

Chemical Property:

• PSA: 157.72000
• LogP: 3.66140
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 523.26037382
• Heavy Atom Count: 36
• Complexity: 833

Purity/Quality:

95-99% ^*data from raw suppliers

EpothiloneF >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CCCC2(C(O2)CC(OC(=O)CC(C(C(=O)C(C1O)C)(C)C)O)C(=CC3=CSC(=N3)CO)C)C
• Isomeric SMILES: C[C@H]1CCC[C@@]2([C@@H](O2)C[C@H](OC(=O)C[C@@H](C(C(=O)[C@@H]([C@H]1O)C)(C)C)O)/C(=C/C3=CSC(=N3)CO)/C)C
• Uses: Epothilone F is a related compound of Epothilones, which are a novel class of antineoplastic agents with antitubulin activity. In addition, Epothilones utilize a similar mechanism of action to that of taxanes and are less susceptible to multidrug resistance caused by P-glycoprotein. Studies showed that Epothilones exhibit antitumor activity against human cancer cells that are taxane-resistant.

Technology Process of epothilone F

There total 22 articles about epothilone F 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: 78.0%

epothilone B-N-oxide → Epothilone F (208518-52-9)

Guidance literature:

epothilone B-N-oxide; With 2,6-dimethylpyridine; trifluoroacetic anhydride; In dichloromethane; at 75 ℃; for 0.166667h;

With ammonia; In tetrahydrofuran; at 45 ℃; for 0.166667h;

DOI:10.1002/(sici)1521-3773(19990712)38:13/14<1971::aid-anie1971>3.0.co;2-x

Reference yield: 68.0%

Acetic acid 4-[(E)-2-((1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-5,9-dioxo-4,17-dioxa-bicyclo[14.1.0]heptadec-3-yl)-propenyl]-thiazol-2-ylmethyl ester → Epothilone F (208518-52-9)

Guidance literature:

With ammonia; In methanol; at 40 ℃; for 0.05h;

DOI:10.1002/(sici)1521-3773(19990712)38:13/14<1971::aid-anie1971>3.0.co;2-x

Reference yield: 64.0%

2-hydroxymethyl-4-tri-n-butylstannylthiazole (204513-18-8) + epothilone B (252981-53-6) → Epothilone F (208518-52-9)

Guidance literature:

With triethylamine; dichloro bis(acetonitrile) palladium(II); In N,N-dimethyl-formamide; at 25 ℃; for 24h;

DOI:10.1002/1521-3765(20000804)6:15<2783::AID-CHEM2783>3.0.CO;2-B

upstream raw materials:

2-hydroxymethyl-4-tri-n-butylstannylthiazole

epothilone B

21-hydroxy-12,13-desoxyepothilone B

(Z)-(4S,7R,8S,9S,16S)-8-Hydroxy-16-[(E)-2-(2-hydroxymethyl-thiazol-4-yl)-1-methyl-vinyl]-5,5,7,9,13-pentamethyl-4-triethylsilanyloxy-oxacyclohexadec-13-ene-2,6-dione

Refernces

• 1、 Chul Bom Lee,Wu,Zhang,Chappell,Stachel,Chou,Guan,Danishefsky. "Insights into long-range structural effects on the stereochemistry of aldol condensations: A practical total synthesis of desoxyepothilone F". . p. 5249 - 5259. Retrieved 2007/10/03.
• 2、 H?fle, Gerhard,Glaser, Nicole,Kiffe, Michael,Hecht, Hans-Jürgen,Sasse, Florenz,Reichenbach, Hans. "N-oxidation of epothilone A-C and O-acyl rearrangement to C-19- and C- 21-substituted epothilones". . p. 1971 - 1974. Retrieved 2007/10/03.