2787-09-9

Usage

Uses

DL-Chloramphenicol is an antibiotic drug.

Upstream product

• 513-96-2 3,3,3-trichloro-2-hydroxy-propionitrile 
• 119-62-0 (+/-)-threo-1-(4-nitro-phenyl)-2-amino-1,3-propanediol 
• 116-54-1 dichloroacetic acid methyl ester 
• 119-62-0 (1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol 
• 872302-03-9 dichloroacetyl-phosphorous acid diethyl ester 
• 26367-75-9 chloramphenicol 
• 33485-03-9 (1RS,2RS)-2-(2,2-dichloro-acetylamino)-1-(4-nitro-phenyl)-1,3-bis-nitryloxy-propane 
• 6158-95-8 (S)-2-(2,2-dichloro-acetylamino)-3-hydroxy-1-(4-nitro-phenyl)-propan-1-one 
• 683-60-3 sodium isopropylate 
• 555-31-7 aluminum isopropoxide 
• 67-63-0 isopropyl alcohol 
• 76738-28-8 (R)-((R)-2-dichloromethyl-4,5-dihydro-oxazol-4-yl)-(4-nitro-phenyl)-methanol 
• 119-62-0 (1RS,2SR)-2-amino-1-(4-nitro-phenyl)-propane-1,3-diol 
• 13916-40-0 bis-dichloroacetyl-amine 

Downstream Products

• 56-75-7 chloramphenicol 
• 134-90-7 L-threo-chloramphenicol 
• 115082-34-3 dichloroacetic acid-[4t-(4-nitro-phenyl)-2ξ-oxo-2λ⁴-[1,3,2]dioxathian-5r-ylamide] 
• 115082-34-3 dichloroacetic acid-[4c-(4-nitro-phenyl)-2ξ-oxo-2λ⁴-[1,3,2]dioxathian-5r-ylamide] 
• 24223-54-9 (RS)-((RS)-2-dichloromethyl-4,5-dihydro-oxazol-4-yl)-(4-nitro-phenyl)-methanol 
• 492-79-5 (1RS,2RS)-3-benzoyloxy-2-(2,2-dichloro-acetylamino)-1-(4-nitro-phenyl)-propan-1-ol 
• 530-43-8 (1RS,2RS)-2-(2,2-dichloro-acetylamino)-1-(4-nitro-phenyl)-3-palmitoyloxy-propan-1-ol 
• 807295-94-9 (2R,3R)-2-amino-3-dichloroacetoxy-3-(4-nitro-phenyl)-propan-1-ol 
• 99860-58-9 (1R,2R)-2-amino-3-dichloroacetoxy-1-(4-nitro-phenyl)-propan-1-ol 
• 33485-06-2 dichloroacetic acid-[(1RS,2SR)-2-chloro-1-chloromethyl-2-(4-nitro-phenyl)-ethylamide] 
• 108717-03-9 (1RS,2SR)-3-benzoyloxy-1-chloro-2-(2,2-dichloro-acetylamino)-1-(4-nitro-phenyl)-propane 
• 103854-92-8 (+/-)-4r-chloromethyl-2-dichloromethyl-5t-(4-nitro-phenyl)-4,5-dihydro-oxazole 
• 575-17-7 (+/-)-[2-dichloromethyl-5t-(4-nitro-phenyl)-4,5-dihydro-oxazol-4r-yl]-methanol 
• 119-62-0 (+/-)-threo-1-(4-nitro-phenyl)-2-amino-1,3-propanediol 

Relevant academic research and scientific papers

Oxidant controlled regio- and stereodivergent azidohydroxylation of alkenes via I2 catalysis

A novel, I2 catalyzed regio- and stereodivergent vicinal azidohydroxylation of alkenes leading to 1,2-azidoalcohols in high yields (up to 92%) and excellent dr (up to 98%) has been developed. This unprecedented transformation employs NaN3 and DMF as N- and O-nucleophiles respectively. The role of DMF as the O-source in the reaction has been unequivocally proven by 18O labelling studies.

Direct synthesis of β-hydroxy-α-amino acids via diastereoselective decarboxylative aldol reaction

A straightforward metal-free synthesis of anti-β-hydroxy-α-amino acids is described. The organic base-mediated decarboxylative aldol reaction of cheap, readily available α-amidohemimalonates with various aldehydes afforded under very mild conditions anti-β-hydroxy-α-amido esters in high yields and complete diastereoselectivity. Simple one-pot subsequent transformations enabled the corresponding anti-β-hydroxy-α-amino acids or in a few examples their syn diastereomers to be obtained directly using epimerization conditions.

Organocatalytic aziridine synthesis using F+ salts

This paper describes a unique application of the fluoronium cation (F +) as an organocatalyst for mediating the reaction between N-substituted imines and ethyl diazoacetate affording excellent yields of N-substituted aziridines.

Synthesis of chloramphenicol via a new intermediate 4-para-nitrophenyl- 5-formamido-1,3-dioxane

4-Phenyl-5-amino-1,3-dioxane 4, obtained from β-bromo styrene 2 was protected as formamido derivative 5. Nitration of 5 followed by regioselective acylative cleavage of the nitro product 12 gave N-formyl-N- acetyl hemiacetal diacetate 16, which on sequential base and acid hydrolysis followed by dichloroacetylation gave chloramphenicol 1.

REGIOSELECTIVE ACYLATIVE CLEAVAGE OF CYCLIC FORMAL OF CHLORAMPHENICOL

The amide 6 has been synthesised by reacting the amine 3 with dichloroketene in situ.This amide 6 on nitration gave formal 7, which when reacted with acetic anhydride and p-toluene sulfonic acid underwent regioselective cleavage of the dioxane ring to furnish the hemiacetal 11.This on treatment with methanol-water-ammonia yielded chloramphenicol 2.