Pumiliotoxin A

Base Information

• Chemical Name: Pumiliotoxin A
• CAS No.: 67054-00-6
• Molecular Formula: C19H33NO2
• Molecular Weight: 307.475
• DSSTox Substance ID: DTXSID80897238
• Nikkaji Number: J794.478K
• Wikidata: Q104396334
• ChEMBL ID: CHEMBL145948
• Mol file: 67054-00-6.mol

Synonyms:alkaloid 307A from Dendrobates;pumiliotoxin A

Chemical Property of Pumiliotoxin A

Chemical Property:

• Vapor Pressure: 1.93E-09mmHg at 25°C
• Boiling Point: 436.2°C at 760 mmHg
• Flash Point: 196.7°C
• PSA: 43.70000
• Density: 1.04g/cm³
• LogP: 3.21320
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 307.251129295
• Heavy Atom Count: 22
• Complexity: 443

Purity/Quality:

PUMILIOTOXIN A 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C(=CCC(C)C=C1CC(C2CCCN2C1)(C)O)C)O
• Isomeric SMILES: CC[C@@H](/C(=C/C[C@@H](C)/C=C\1/C[C@]([C@@H]2CCCN2C1)(C)O)/C)O

Technology Process of Pumiliotoxin A

There total 36 articles about Pumiliotoxin A 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: 85.0%

(8S,8aS)-8-hydroxy-8-methyl-(6Z)-<(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-4-octenylidene>octahydroindolizidine (98088-45-0) → (+)-pumiliotoxin A (67054-00-6)

Guidance literature:

With ammonia; lithium; In tetrahydrofuran;

DOI:10.1021/ja961641q

Reference yield: 75.0%

(8S,8aS)-6-[(E)-(S)-6-Benzyloxy-2,5-dimethyl-oct-4-en-(Z)-ylidene]-8-methyl-octahydro-indolizin-8-ol (98088-45-0) → (+)-pumiliotoxin A (67054-00-6)

Guidance literature:

With ammonia; lithium; In tetrahydrofuran; at -78 ℃;

DOI:10.1021/jo00219a060

Reference yield: 71.0%

(6Z,8S,8aS)-6-[(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-4-octenylidene]-8-{[tert-butyl(dimethyl)silyl]oxy}-8-methyloctahydroindolizine (251976-94-0) → (+)-pumiliotoxin A (67054-00-6)

Guidance literature:

(6Z,8S,8aS)-6-[(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-4-octenylidene]-8-{[tert-butyl(dimethyl)silyl]oxy}-8-methyloctahydroindolizine; With triethylamine tris(hydrogen fluoride);

With ammonia; lithium; In methanol;

DOI:10.1016/S0022-328X(02)01160-9

upstream raw materials:

(8S,8aS)-6-[(E)-(S)-6-Benzyloxy-2,5-dimethyl-oct-4-en-(Z)-ylidene]-8-methyl-octahydro-indolizin-8-ol

(8S,8aS)-8-hydroxy-8-methyl-(6Z)-<(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-4-octenylidene>octahydroindolizidine

(6Z,8S,8aS)-6-[(2R,4E,6S)-6-(benzyloxy)-2,5-dimethyl-4-octenylidene]-8-{[tert-butyl(dimethyl)silyl]oxy}-8-methyloctahydroindolizine

(3S)-3-(benzyloxy)-2-pentanone