Asteltoxin

Base Information

• Chemical Name: Asteltoxin
• CAS No.: 79663-49-3
• Molecular Formula: C₂₃H₃₀O₇
• Molecular Weight: 418.487
• DSSTox Substance ID: DTXSID101046614
• Nikkaji Number: J37.387G
• Metabolomics Workbench ID: 100259
• ChEMBL ID: CHEMBL3758613
• Mol file: 79663-49-3.mol

Synonyms:asteltoxin

Chemical Property of Asteltoxin

Chemical Property:

• Vapor Pressure: 1.53E-17mmHg at 25°C
• Refractive Index: 1.5800 (estimate)
• Boiling Point: 612.1°C at 760 mmHg
• PKA: 13.49±0.70(Predicted)
• Flash Point: 208.5°C
• PSA: 98.36000
• Density: 1.24g/cm³
• LogP: 2.73430
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 418.19915329
• Heavy Atom Count: 30
• Complexity: 837

Purity/Quality:

99% ^*data from raw suppliers

Asteltoxin ≥97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1C(C2(C(C(OC2O1)C=CC=CC=CC3=C(C(=CC(=O)O3)OC)C)O)C)(C)O
• Isomeric SMILES: CC[C@@H]1[C@]([C@]2([C@H]([C@H](O[C@H]2O1)/C=C/C=C/C=C/C3=C(C(=CC(=O)O3)OC)C)O)C)(C)O

Technology Process of Asteltoxin

There total 66 articles about Asteltoxin 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: 87.0%

astelotoxin bis(trimethylsilyl) ether (536737-95-8) → asteltoxin (79663-49-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 4 ℃; for 36h;

DOI:10.1021/ja034332q

Reference yield: 82.0%

4(R,S),6(R,S)-dihydroxy-5(R,S),6-dimethyl-7(R,S)-ethyl-3(R,S)-(5-hydroxy-6-(4-methoxy-5-methyl-α-pyron-6-yl)-(E,E)-hexa-1,3-dien-1-yl)-1(S,R)-2,8-dioxabicyclo<3.3.0>octane (90623-39-5) → (+/-)-asteltoxin (79663-49-3,87480-12-4)

Guidance literature:

With dmap; triethylamine; p-toluenesulfonyl chloride; In dichloromethane; for 12h;

DOI:10.1021/ja00327a020

Reference yield: 73.0%

(1R,3R,4R,5R,6R,7R)-3-ethyl-4,6-dihydroxy-7-<(1E,3E,5RS)-5-hydroxy-6-(4-methoxy-5-methyl-2-pyron-6-yl)hexa-1,3-dienyl>-4,5-dimethyl-2,8-dioxabicyclo<3.3.0>octane (90623-39-5) → asteltoxin (79663-49-3)

Guidance literature:

With dmap; triethylamine; p-toluenesulfonyl chloride; In dichloromethane; for 18h; Ambient temperature;

DOI:10.1016/S0040-4020(01)82015-9

upstream raw materials:

(1R,3R,4R,5R,6R,7R)-3-ethyl-4,6-dihydroxy-7-<(1E,3E,5RS)-5-hydroxy-6-(4-methoxy-5-methyl-2-pyron-6-yl)hexa-1,3-dienyl>-4,5-dimethyl-2,8-dioxabicyclo<3.3.0>octane

(E)-3-((2R,3R,3aR,4R,5R,6aS)-5-Ethyl-3,4-dihydroxy-3a,4-dimethyl-hexahydro-furo[2,3-b]furan-2-yl)-propenal

astelotoxin bis(trimethylsilyl) ether

(1S,3R,4R,5R,6R,7R)-5,6-dimethyl-7-ethyl-3-(hydroxymethyl)-4-(4-methoxybenzyloxy)-2,8-dioxabicyclo[3.3.0]octan-6-ol

Refernces

• 1、 Tadano, Kin-ichi,Yamada, Hirohiko,Idogaki, Yoko,Ogawa, Seiichiro,Suami, Tetsuo. "TOTAL SYNTHESIS OF (+)-ASTELTOXIN". . p. 2353 - 2366. Retrieved 2007/10/02.