Pederin

Base Information

• Chemical Name: Pederin
• CAS No.: 27973-72-4
• Molecular Formula: C25H45 N O9
• Molecular Weight: 503.63
• NSC Number: 114781
• UNII: B8F7J348GJ
• DSSTox Substance ID: DTXSID90182248
• Wikipedia: Pederin
• Wikidata: Q8214251
• Metabolomics Workbench ID: 98896
• Mol file: 27973-72-4.mol

Synonyms:N-((6-(2,3-dimethoxypropyl)tetrahydro-4-hydroxy-5,5-dimethyl-2H-pyran-2-yl)methoxymethyl)tetrahydro-alpha-hydroxy-2-methoxy-5,6-dimethyl-4-methylene-2H-pyran-2-acetamide;paederine;pederin;pederine

Chemical Property of Pederin

Chemical Property:

• Vapor Pressure: 7.48E-19mmHg at 25°C
• Melting Point: 112-112.5°
• Boiling Point: 636°Cat760mmHg
• Flash Point: 338.5°C
• PSA: 124.94000
• Density: 1.15g/cm³
• LogP: 1.76680
• XLogP3: 1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 11
• Exact Mass: 503.30943201
• Heavy Atom Count: 35
• Complexity: 717

Purity/Quality:

99%, ^*data from raw suppliers

PEDERIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(OC(CC1=C)(C(C(=O)NC(C2CC(C(C(O2)CC(COC)OC)(C)C)O)OC)O)OC)C
• Isomeric SMILES: C[C@H]1[C@H](O[C@](CC1=C)([C@@H](C(=O)N[C@H]([C@@H]2C[C@H](C([C@H](O2)C[C@@H](COC)OC)(C)C)O)OC)O)OC)C

Technology Process of Pederin

There total 46 articles about Pederin 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: 92.0%

(+/-)-pederin dibenzoate (111194-21-9,123483-10-3) → (+/-)-pederin (27973-72-4,85249-20-3,111212-06-7)

Guidance literature:

With lithium hydroxide; In methanol; at 50 ℃; for 5h;

DOI:10.1016/S0040-4020(01)81981-5

Reference yield: 92.0%

→ (+)-pederine (27973-72-4)

Guidance literature:

With lithium hydroxide; In methanol; at 50 ℃; for 5h;

DOI:10.1016/S0040-4039(00)97415-X

Reference yield: 89.0%

(+)-dibenzoylpederin (123483-10-3) → (+)-pederine (27973-72-4)

Guidance literature:

With lithium hydroxide; In methanol; for 3h; Ambient temperature;

DOI:10.1016/S0040-4020(01)86075-0

upstream raw materials:

(+/-)-pederin dibenzoate

Benzoic acid (S)-chlorocarbonyl-((2R,4S,5R,6R)-2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-methyl ester

C₄₅H₅₉NO₁₁Se

(+/-)-benzoylselenopederic acid

Downstream raw materials:

(+)-dibenzoylpederin

Refernces

• 1、 Jarowicki,Kocienski,Marczak,Willson. "A synthesis of (+)-pederin. The metallated dihydropyran approach". . p. 3433 - 3436. Retrieved 1990.
• 2、 Wu, Fanghui,Green, Michael E.,Floreancig, Paul E.. "Total synthesis of pederin and analogues". . p. 1131 - 1134. Retrieved 2011/04/22.
• 3、 Jewett, John C.,Rawal, Viresh H.. "Total synthesis of pederin". . p. 6502 - 6504. Retrieved 2008/09/18.