(8R,16R)-(-)-pyrenophorin

Base Information

• Chemical Name: (8R,16R)-(-)-pyrenophorin
• CAS No.: 5739-85-5
• Molecular Formula: C16H20 O6
• Molecular Weight: 308.331
• Wikidata: Q105209976
• ChEMBL ID: CHEMBL2269363
• Mol file: 5739-85-5.mol

Synonyms:CHEMBL2269363;SCHEMBL11911415;(8R,16R)-(-)-pyrenophorin

Chemical Property of (8R,16R)-(-)-pyrenophorin

Chemical Property:

• Vapor Pressure: 5.91E-12mmHg at 25°C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 86.74000
• Density: 1.37g/cm³
• LogP: 1.67440
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 308.12598835
• Heavy Atom Count: 22
• Complexity: 457

Purity/Quality:

99%, ^*data from raw suppliers

PYRENOPHORIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(=O)C=CC(=O)OC(CCC(=O)C=CC(=O)O1)C
• Isomeric SMILES: C[C@H]1OC(=O)/C=C/C(=O)CC[C@H](OC(=O)/C=C/C(=O)CC1)C

Technology Process of (8R,16R)-(-)-pyrenophorin

There total 73 articles about (8R,16R)-(-)-pyrenophorin 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: 98.0%

(10R,22R)-10,22-dimethyl-1,4,9,14,17,21-hexaoxadispiro[4.7.4.7]tetracosa-6,18-diene-8,20-dione → (3E,8R,11E,16R)-8,16-Dimethyl-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetraone (5739-85-5)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; for 20h; Ambient temperature;

DOI:10.1246/cl.1994.1083

Reference yield: 93.0%

(3E,8R,11E,16R)-5,13-Dihydroxy-8,16-dimethyl-1,9-dioxacyclohexadeca-3,11-diene-2,10-dione (22248-41-5,102679-55-0,135026-78-7,155326-45-7) → (3E,8R,11E,16R)-8,16-Dimethyl-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetraone (5739-85-5)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1246/cl.1994.1103

Reference yield: 90.0%

(5S,8R,13S,16R)-5,13-dihydroxy-8,16-dimethyl-1,9-dioxacyclohexadeca-3,11-diene-2,10-dione (102679-55-0,135026-78-7,22248-41-5,155326-45-7) → (3E,8R,11E,16R)-8,16-Dimethyl-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetraone (5739-85-5)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; at 20 ℃; for 50h;

DOI:10.1002/ejoc.200800404

upstream raw materials:

Trifluoro-acetic acid 8,16-dimethyl-2,5,10,13-tetraoxo-11-(2,2,2-trifluoro-acetoxy)-1,9-dioxa-cyclohexadec-3-yl ester

(E)-7-(tert-Butyl-dimethyl-silanyloxy)-4-oxo-oct-2-enoic acid methyl ester

(+/-)-7-hydroxyoct-2-enoic acid

(3E,11E)-8,16-Dimethyl-5,13-bis-trimethylsilanyloxy-1,9-dioxa-cyclohexadeca-3,11-diene-2,10-dione

Refernces

• 1、 Ramakrishna, Kolluri,Sreenivasulu, Reddymasu,Vidavalur, Siddaiah,Reddy, Boggu Jagan Mohan. "Stereoselective total synthesis of (-)-pyrenophorin". . p. 693 - 697. Retrieved 2016.
• 2、 Zhang, Wen,Krohn, Karsten,Egold, Hans,Draeger, Siegfried,Schulz, Barbara. "Diversity of antimicrobial pyrenophorol derivatives from an endophytic fungus, Phoma sp.". experimental part. p. 4320 - 4328. Retrieved 2009/04/11.