439797-74-7

Upstream product

• 217661-62-6 [(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-hydroxy-2-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 1009093-14-4 ((1R,2R)-2-hydroxy-1-hydroxymethyl-2-phenylethyl)carbamic acid tert-butyl ester 
• 100-58-3 phenylmagnesium bromide 
• 217661-64-8 Acetic acid (1R,2R)-3-acetoxy-2-tert-butoxycarbonylamino-1-phenyl-propyl ester 

Downstream Products

• 56-75-7 chloramphenicol 
• 119-62-0 (1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol 
• 51259-82-6 (1R,2R)-1,3-diacetoxy-2-acetylamino-1-(4-nitro-phenyl)-propane 
• 111136-67-5 (1R,2R)-2-acetamido-1-phenylpropane-1,3-diyl diacetate 

Relevant academic research and scientific papers

Stereoselective synthesis of chloramphenicol from D-serine

An efficient synthesis of the widely used antibiotic chloramphenicol (1) is described. The key step in the synthesis involves chelation-controlled addition of phenylmagnesium bromide to a suitably protected D-serinal derivative, affording the pivotal D-threo 1,2-amino alcohol intermediate 3 in a highly stereoselective manner.