105882-69-7

Basic information

• Product Name: LY 267108
• Synonyms: LY 267108;(2R,3R,6R,7S,8S,9R,10R)-7-[(2,6-Dideoxy-3-C-Methyl-3-O-Methyl-α-L-ribo-hexopyranosyl)oxy]-3-[(1R,2R)-1,2-dihydroxy-1-Methylbutyl]-2,6,8,10,12-pentaMethyl-9-[[3,4,6-trideoxy-3-(diMethylaMino)-β-D-xylo-hexopyranosyl]oxy]-4,13-dioxabicyclo[8.2.1]tridec-12-en-5-one;8,9-Anhydropseudo-erythroMycin A-6,9-heMiketal;(2R,3R,6R,7S,8S,9R,10R)-7-[(2,6-Dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl)oxy]-3-[(1R,2R)-1,2-dihydroxy-1-methylbutyl]-2,6,8,10,12-pentamethyl-9-[[3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl]oxy]-4,13-dioxabicyclo[8.2.1]tridec-12-en-5-one;NMIWBQUQCOMGHJ-XWVSLMRSSA-N
• CAS NO: 105882-69-7
• Molecular Formula: C₃₇H₆₅NO₁₂
• Molecular Weight: 715.916
• Product Categories: Chromatography;Drugs&Metabolites;Forensic and Veterinary Standards;Neat CompoundsAnalytical Standards;Pharmacology Standards;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 105882-69-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 127.0-130.0 °C
• Boiling Point: 810.7±65.0 °C(Predicted)
• Appearance: /
• Density: 1.20±0.1 g/cm3(Predicted)
• Storage Temp.: −20°C
• PKA: 13.45±0.70(Predicted)
• CAS DataBase Reference: LY 267108(CAS DataBase Reference)
• NIST Chemistry Reference: LY 267108(105882-69-7)
• EPA Substance Registry System: LY 267108(105882-69-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 105882-69-7(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 105882-69-7 differently. You can refer to the following data:
1. Pseudoerythromycin A enol ether is a degradation product of erythromycin formed by a complex internal rearrangement of erythromycin A on exposure to neutral to weakly alkaline conditions. The C6–OH forms an internal enol ether with the C9 ketone of erythromycin, while the C11-OH attacks the carbonyl of the lactone to reduce the macrocycle from a 14- to an 11-membered macrolide. Synthetically, pseudoerythromycin A enol ether is prepared by reacting erythromycin enol ether with carbonate. Pseudoerythromycin A enol ether is devoid of antibiotic activity but is an important analytical standard for erythromycin A stability studies.
2. Pseudo Erythromycin A Enol Ether (Erythromycin EP Impurity F) is an Erythromycin impurity.
3. Erythromycin impurity.

Upstream product

• 105900-46-7 pseudoerythromycin A 6,9-hemiketal 
• 114-07-8 erythromycin 
• 33396-29-1 8,9-anhydroerythromycin A 6,9-hemiacetal 
• 114-07-8 erythromycin A 
• 33396-29-1 erythromycin A enol ether 

Downstream Products

• 123-38-6 propionaldehyde 
• 105882-72-2 (2S,6S,7R,8S,9R,10S)-3-Acetyl-9-((2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-7-((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-2,6,8,10,12-pentamethyl-4,13-dioxa-bicyclo[8.2.1]tridec-1⁽¹²⁾-en-5-one 
• 33396-29-1 erythromycin A enol ether 
• 23893-13-2 erythromycin A 6,9;9,12-spiroketal 

Relevant articles and documents

Synthesis of ring-contracted erythromycin a derivatives via microwave-assisted intramolecular transesterification

The synthesis of ring-contracted derivatives of erythromycin A via intramolecular transesterification under microwave irradiation of 8,9-anhydro-erythromycin A 6,9-hemiketal and its derivatives is described. It was found that microwave irradiation could s

Translactonization of erythromycin a during oximation: Mixture analysis and reaction monitoring by NMR

Oximation of erythromycin A with hydroxylamine hydrochloride and sodium acetate in methanol led to the formation of pseudoerythromycin A enol ether with erythromycin A oxime as analysed by detailed two-dimensional NMR spectroscopy in the mixture along with traces of 8,9-anhydroerythromycin A 6,9-hemiketal and erythromycin A 6,9:9,12-spiroketal. The formation of the degraded products was established by performing in situ 13C NMR spectroscopy. The analysis suggests that pseudoerythromycin A enol ether is formed by the translactonization of erythromycin A enol ether which forms as a result of acid degradation. Copyright

Translactonization in Erythromycins

When erythromycin A is heated in diethylamine-acetic acid, an erythromycin hemiketal is obtained, which can be further transformed into a new enol ether and spiroketal.The new enol ether is also obtained in equilibrium with the normal one on heating erythromycin A or B in pyridine-acetic acid.The novel compounds, which will be called pseudoerythromycin derivatives, are characterized by a translactonization between the C11-hydroxyl and the lactone group.Their structure was proved by mass and 1H and 13C NMR spectrometry, by acetylation experiments, and by degradation with lead tetraacetate.