Erythromycin A Enol Ether

Base Information

• Chemical Name: Erythromycin A Enol Ether
• CAS No.: 33396-29-1
• Molecular Formula: C37H65 N O12
• Molecular Weight: 715.91
• Mol file: 33396-29-1.mol

Synonyms:6,15-Dioxabicyclo[10.2.1]pentadecane,erythromycin deriv.; 8,9-Anhydroerythromycin A 6,9-hemiketal; BRL 46357ER; EM201; Erythromycin A enol ether; Erythromycin enol ether; ME 4

Chemical Property of Erythromycin A Enol Ether

Chemical Property:

• Vapor Pressure: 5.76E-29mmHg at 25°C
• Melting Point: 133-1350C
• Boiling Point: 791.6°Cat760mmHg
• PKA: 13.45±0.70(Predicted)
• Flash Point: 432.6°C
• PSA: 165.84000
• Density: 1.2g/cm³
• LogP: 2.89230
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

Purity/Quality:

98%Min ^*data from raw suppliers

Erythromycin A enol ether ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: Impurity E Erythromycin A enol ether is a degradation product of erythromycin formed under acidic conditions by C6–OH internal attack on the C9 ketone to produce a cyclic enol ether. The rearrangement results in a loss of antibiotic activity. This single reaction was the prime driver for the development of second and third generation erythromycins. Erythromycin A enol ether is an important standard for stability studies. Erythromycin A Enol Ether (Erythromycin EP Impurity E) is an impurity of Erythromycin.

Technology Process of Erythromycin A Enol Ether

There total 9 articles about Erythromycin A Enol Ether 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: 73.0%

erythromycin A → 8,9-anhydroerythromycin A 6,9-hemiacetal (33396-29-1)

Guidance literature:

With acetic acid; at 20 ℃; for 0.5h;

DOI:10.1016/j.bmcl.2007.08.068

Reference yield: 68.0%

erythromycin (114-07-8) → 8,9-anhydroerythromycin A 6,9-hemiacetal (33396-29-1)

Guidance literature:

With acetic acid; for 1h; Ambient temperature;

DOI:10.1021/jo00228a038

Reference yield: 18.5%

erythromycin A (114-07-8) → pseudoerythromycin A enol ether (105882-69-7) + erythromycin A enol ether (33396-29-1)

Guidance literature:

With pyridine; acetic acid; at 70 ℃; for 24h;

DOI:10.1021/jo00382a004

upstream raw materials:

erythromycin

erythromycin A

pseudoerythromycin A enol ether

pseudoerythromycin A 6,9-hemiketal

Downstream raw materials:

erythromycin A 6,9;9,12-spiroketal

pseudoerythromycin A enol ether

anhydroerythromycin A

8,9-anhydropseudoerythromycin A 6,9-hemiketal

Refernces

• 1、 Heggelund, Audun,Undheim, Kjell. "Synthesis of 8-fluorinated erythromycin cyclic 2',3'-carbamates". . p. 1903 - 1913. Retrieved 2009.
• 2、 Sugawara, Akihiro,Sunazuka, Toshiaki,Hirose, Tomoyasu,Nagai, Kenichiro,Yamaguchi, Yukie,Hanaki, Hideaki,Sharpless, K. Barry,Omura, Satoshi. "Design and synthesis via click chemistry of 8,9-anhydroerythromycin A 6,9-hemiketal analogues with anti-MRSA and -VRE activity". . p. 6340 - 6344. Retrieved 2008/09/17.