Fumagillol

Base Information

• Chemical Name: Fumagillol
• CAS No.: 108102-51-8
• Molecular Formula: C₁₆H₂₆O₄
• Molecular Weight: 282.38
• NSC Number: 9665
• UNII: 409OS4DE8W
• Nikkaji Number: J458.430I
• Wikidata: Q27105155
• Metabolomics Workbench ID: 52748
• ChEMBL ID: CHEMBL137317
• Mol file: 108102-51-8.mol

Synonyms:fumagillol

Chemical Property of Fumagillol

Chemical Property:

• Vapor Pressure: 1.08E-07mmHg at 25°C
• Melting Point: 54-56 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 389.9°Cat760mmHg
• PKA: 14.21±0.60(Predicted)
• Flash Point: 189.6°C
• PSA: 54.52000
• Density: 1.13g/cm³
• LogP: 2.05510
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 282.18310931
• Heavy Atom Count: 20
• Complexity: 417

Purity/Quality:

99%, ^*data from raw suppliers

Fumagillol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1C(O1)(C)C2C(C(CCC23CO3)O)OC)C
• Isomeric SMILES: CC(=CC[C@@H]1[C@@](O1)(C)[C@H]2[C@@H]([C@@H](CC[C@]23CO3)O)OC)C
• Uses: Fumagillol is an analog of Fumagillin (F862650), a compound isolated from the fungus Aspergillus fumigatus. Fumagillin is an antimicrobial agent used in the treatment of microsporidiosis. Fumagillin shows promise as both an an anti-infective and antiangiogenic agent.

Technology Process of Fumagillol

There total 27 articles about Fumagillol 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: 94.0%

Fumaginone (132746-88-4) → fumagillol (35903-52-7,128656-25-7,132746-73-7,108102-51-8)

Guidance literature:

With potassium tri-sec-butyl-borohydride; In tetrahydrofuran; at -78 ℃;

DOI:10.1002/anie.200502826

Reference yield: 90.0%

fumagillin (23110-15-8,297-95-0) → fumagillol (35903-52-7,128656-25-7,132746-73-7,108102-51-8)

Guidance literature:

With water; sodium hydroxide; In methanol; at 0 - 40 ℃;

DOI:10.1021/ol4035269

Reference yield: 89.0%

triphenylphosphonio-1-methylethanide (16666-80-1) → fumagillol (35903-52-7,128656-25-7,132746-73-7,108102-51-8)

Guidance literature:

With methanol; potassium carbonate;

DOI:10.1021/ja990784k

upstream raw materials:

triphenylphosphonio-1-methylethanide

fumagillin

Fumaginone

(R)-4-hydroxy-1,4-dioxa-spiro[4.5]decan-8-one

Downstream raw materials:

(1R)-2c-((1S,2Ξ)-1,2-epoxy-1,5-dimethyl-hexyl)-3t-methoxy-1-methyl-cyclohexane-1r,4t-diol

6-O-(2-carboxybenzoyl)fumagillol

(3R,4S,5S,6R)-4-((2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl)-5-(oxo-λ⁶-methyl)-1-oxaspiro[2.5]octan-6-yl acetylcarbamate

6-O-chloroacetylcarbamoylfumagillol

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