864529-27-1

Basic information

• Product Name: ChloraMphenicol 2-(O-tert-ButyldiMethylsilyl)Methyl 1-Acetate
• Synonyms: ChloraMphenicol 2-(O-tert-ButyldiMethylsilyl)Methyl 1-Acetate;N-[(1R,2R)-2-(Acetyloxy)-1-(O-tert-butyldiMethylsilyl)Methyl-2-(4-nitrophenyl)ethyl]-2,2-dichloro-acetaMide;N-[(1R,2R)-2-(Acetyloxy)-1-[[[(1,1-diMethylethyl)diMethylsilyl]oxy]Methyl]-2-(4-nitrophenyl)ethyl]-2,2-dichloro-acetaMide.
• CAS NO: 864529-27-1
• Molecular Formula: C₁₉H₂₈Cl₂N₂O₆Si
• Molecular Weight: 479.42692
• Product Categories: Amines;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 864529-27-1.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: ChloraMphenicol 2-(O-tert-ButyldiMethylsilyl)Methyl 1-Acetate(CAS DataBase Reference)
• NIST Chemistry Reference: ChloraMphenicol 2-(O-tert-ButyldiMethylsilyl)Methyl 1-Acetate(864529-27-1)
• EPA Substance Registry System: ChloraMphenicol 2-(O-tert-ButyldiMethylsilyl)Methyl 1-Acetate(864529-27-1)

Safety Data

• Hazardous Substances Data: 864529-27-1(Hazardous Substances Data)

Usage

Chemical Properties

Oil

Uses

ChloraMphenicol 2-(O-tert-ButyldiMethylsilyl)Methyl 1-Acetate is used in the preparation of Azithromycin (A927000) compounds as antibacterial, anti-proliferative, and antiinflammatory agents.

Upstream product

• 56-75-7 chloramphenicol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 108-24-7 acetic anhydride 
• 864529-25-9 chloramphenicol 

Downstream Products

• 24863-80-7 (1R,2R)-2-[(dichloroacetyl)amino]-3-hydroxy-1-(4-nitrophenyl)propyl acetate 

Relevant articles and documents

Chloramphenicol Derivatives with Antibacterial Activity Identified by Functional Metagenomics

A functional metagenomic approach identified novel and diverse soil-derived DNAs encoding inhibitors to methicillin-resistant Staphylococcus aureus (MRSA). A metagenomic DNA soil library containing 19 200 recombinant Escherichia coli BAC clones with 100 Kb average insert size was screened for antibiotic activity. Twenty-seven clones inhibited MRSA, seven of which were found by LC-MS to possess modified chloramphenicol (Cm) derivatives, including three new compounds whose structures were established as 1-acetyl-3-propanoylchloramphenicol, 1-acetyl-3-butanoylchloramphenicol, and 3-butanoyl-1-propanoylchloramphenicol. Cm was used as the selectable antibiotic for cloning, suggesting that heterologously expressed enzymes resulted in derivatization of Cm into new chemical entities with biological activity. An esterase was found to be responsible for the enzymatic regeneration of Cm, and the gene trfA responsible for plasmid copy induction was found to be responsible for inducing antibacterial activity in some clones. Six additional acylchloramphenicols were synthesized for structure and antibacterial activity relationship studies, with 1-p-nitrobenzoylchloramphenicol the most active against Mycobacterium intracellulare and Mycobacterium tuberculosis, with MICs of 12.5 and 50.0 μg/mL, respectively.

Elucidating absolute configuration of unsaturated alcohols via enantioselective acylation reactions

Enantioselective nucleophilic acylation catalysis provides a simple method of determining absolute configuration for unsaturated alcohols. Extension of this technique to natural products and synthetic compounds, as well as current limitations of this appr