992-69-8

Basic information

• Product Name: erythromycin 2'-acetate
• Synonyms: erythromycin 2'-acetate
• CAS NO: 992-69-8
• Molecular Formula: C₃₉H₆₉NO₁₄
• Molecular Weight: 775.967
• Mol File: 992-69-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 819.9°Cat760mmHg
• Flash Point: 449.7°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 3.74E-31mmHg at 25°C
• Refractive Index: 1.528
• CAS DataBase Reference: erythromycin 2'-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: erythromycin 2'-acetate(992-69-8)
• EPA Substance Registry System: erythromycin 2'-acetate(992-69-8)

Safety Data

• Hazardous Substances Data: 992-69-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C39H69NO14/c1-15-27-39(11,47)32(43)21(4)29(42)19(2)17-37(9,46)34(54-36-31(51-25(8)41)26(40(12)13)16-20(3)49-36)22(5)30(23(6)35(45)52-27)53-28-18-38(10,48-14)33(44)24(7)50-28/h19-24,26-28,30-34,36,43-44,46-47H,15-18H2,1-14H3/t19-,20-,21+,22+,23-,24+,26+,27-,28+,30+,31-,32-,33+,34-,36+,37-,38-,39-/m1/s1

Upstream product

• 75-36-5 acetyl chloride 
• 114-07-8 erythromycin 
• 108-24-7 acetic anhydride 

Downstream Products

• 1379596-16-3 2'-acetyl-3'-phenylthionoformyl-3'-N-desmethylerythromycin A 
• 1253278-95-3 4''-O-(2-chlorophenethyl)carbamoyl erythromycin A 
• 1253278-94-2 4''-O-(4-hydroxyphenethyl)carbamoyl erythromycin A 
• 1253278-93-1 4''-O-(phenethyl)carbamoyl erythromycin A 
• 1253278-92-0 4''-O-(4-methoxybenzyl)carbamoyl erythromycin A 
• 1253278-91-9 4''-O-(4-fluorobenzyl)carbamoyl erythromycin A 
• 1253278-89-5 4''-O-(benzyl)carbamoyl erythromycin A 

Relevant articles and documents

An approach to the site-selective deoxygenation of hydroxy groups based on catalytic phosphoramidite transfer

Selective: The deoxygenation of simple and complex natural products employing a readily synthesized phosphoramidite and tetrazole catalysts can be executed as a two-step process, without the need to isolate intermediate deoxygenation precursors. Furthermore, a peptide-based tetrazole catalyst controls the site selectivity of deoxyerythromycin synthesis (see scheme), thus overcoming the notorious challenges with unprotected erythromycin A. Copyright

Synthesis and antibacterial activity of novel 4″-O-carbamoyl erythromycin-A derivatives

Novel 4″-O-carbamoyl erythromycin-A derivatives were designed, synthesized, and evaluated for their in-vitro antibacterial activities. All of the 4″-O-carbamoyl derivatives showed excellent activity against erythromycin-susceptible Staphylococcus aureus ATCC25923, Streptococcus pyogenes, and Streptococcus pneumoniae ATCC49619. Most of the 4″-O-arylalkylcarbamoyl derivatives displayed potent activity against erythromycin-resistant S. pneumoniae encoded by the mef gene and greatly improved activity against erythromycin-resistant S. pneumoniae encoded by the erm gene or the erm and mef genes. In particular, the 4″-O-arylalkyl derivatives 4c-4e and 4g were found to possess the most potent activity against all the tested erythromycin-susceptible strains, which were comparable to those of erythromycin, clarithromycin, or azithromycin. 4″-O-Arylalkyl derivatives 4e and 4g were the most effective against erythromycin-resistant S. pneumoniae encoded by the mef gene (0.25 and 0.25 μg/mL). 4″-O-Arylalkyl derivatives 4a and 4b exhibited significantly improved activity against erythromycin-resistant S. pneumoniae encoded by the erm gene. In contrast, the 4″-O-alkylcarbamoyl derivatives hardly showed improved activity against all the tested erythromycin-resistant strains.

Synthesis and biological investigation of new 4″-malonyl tethered derivatives of erythromycin and clarithromycin

A new approach to 4″-substituted derivatives of erythromycin and clarithromycin was developed by converting them into corresponding 4″-malonic monoesters. Subsequent carbodiimide coupling with alcohols and amines provided new macrolide derivatives that are capable of binding to 50S ribosomal subunits and inhibiting protein synthesis in cell-free system.