Antibiotic UCF76 C

Base Information

• Chemical Name: Antibiotic UCF76 C
• CAS No.: 68930-68-7
• Molecular Formula: C₁₈H₁₆O₆
• Molecular Weight: 328.321
• Wikidata: Q103816458
• Mol file: 68930-68-7.mol

Synonyms:Antibiotic UCF76 C;Antibiotic AM 3867I;UCF76 C;AM 3867I

Chemical Property of Antibiotic UCF76 C

Chemical Property:

• Vapor Pressure: 4.6E-16mmHg at 25°C
• Boiling Point: 622°C at 760 mmHg
• Flash Point: 232.7°C
• PSA: 89.90000
• Density: 1.46g/cm³
• LogP: 1.95080
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 328.09468823
• Heavy Atom Count: 24
• Complexity: 635

Purity/Quality:

≥98% （HPLC） ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC1C2=C(C3C(O1)CC(=O)O3)C(=O)C4=C(C2=O)C(=CC=C4)O

Technology Process of Antibiotic UCF76 C

There total 27 articles about Antibiotic UCF76 C 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: 60.0%

(+)-epi-frenolicin B → Frenolicin B (68930-68-7)

Guidance literature:

With sulfuric acid; at 20 ℃; for 0.416667h; Inert atmosphere;

DOI:10.1021/jo3019939

Reference yield: 40.0%

Deoxyfrenolicin (10023-11-7) → Frenolicin B (68930-68-7)

Guidance literature:

With pyridine; oxygen; In methanol; acetonitrile; for 16h; Heating;

DOI:10.1002/hlca.19970800104

Reference yield: 24.0%

(3aR,5S,11bR)-3,3a,5,11b-tetrahydro-7-methoxy-5-propyl-1,4-dioxacyclopent[a]anthracen-2,6,11-trione (216358-09-7) + (3aR,5S,11bR)-3,3a,5,11b-tetrahydro-7-methoxy-5-propyl-1,4-dioxacyclopent[a]anthracen-2,6,11-trione (1404583-65-8) → Frenolicin B (68930-68-7) + (+)-epi-frenolicin B

Guidance literature:

With boron tribromide; In dichloromethane; at -50 - 20 ℃; for 2.5h; Inert atmosphere;

DOI:10.1021/jo3019939

upstream raw materials:

(+/-)-deoxyfrenolicin

(7S,7aS,9R,11S,11aS,11bR)-2,2-Dimethyl-11-propyl-7,8,9,11,11a,11b-hexahydro-7aH-1,3,10-trioxa-benzo[de]anthracene-7,9-diol

((7aS,9R,11S,11aS,11bR)-2,2-Dimethyl-7-oxo-11-propyl-7,8,9,11,11a,11b-hexahydro-7aH-1,3,10-trioxa-benzo[de]anthracen-9-yl)-acetic acid methyl ester

((7R,7aR,9S,11R,11aR,11bS)-7-Hydroxy-2,2-dimethyl-11-propyl-7,8,9,11,11a,11b-hexahydro-7aH-1,3,10-trioxa-benzo[de]anthracen-9-yl)-acetic acid methyl ester

Refernces

• 1、 Donner, Christopher D.. "The divergent asymmetric synthesis of kalafungin, 5-epi-frenolicin B and related pyranonaphthoquinone antibiotics". . p. 377 - 386. Retrieved 2013/01/15.
• 2、 Masquelin, Thierry,Hengartner, Urs,Streith, Jacques. "3. Naphthopyranquinone Antibiotics: Novel Enantioselective Syntheses of Frenolicin B and Some of Its Stereoisomers". . p. 43 - 58. Retrieved 2007/10/03.