185522-98-9

Upstream product

• 5056-07-5 (S)-methyl p-tolyl sulfoxide 
• 39687-95-1 isocyanoacetic acid methyl ester 
• 142722-58-5 (S)-(-)-1-fluoro-3-<(4-methylphenyl)sulphinyl>propan-2-one 

Downstream Products

• 185522-99-0 (2S,3S)-3-Fluoromethyl-2-formylamino-3-hydroxy-4-((S)-toluene-4-sulfinyl)-butyric acid methyl ester 
• 185523-00-6 (2S,3S)-3-Fluoromethyl-2-formylamino-3-hydroxy-4-p-tolylsulfanyl-butyric acid methyl ester 
• 1363368-19-7 4-(4-(4-aminophenyl)buta-1,3-diynyl)-N-((2S,3S)-4-fluoro-3-hydroxy-1-(hydroxyamino)-3-methyl-1-oxobutan-2-yI)benzamide 
• 1363373-74-3 C₂₃H₂₁FN₂O₄ 

Relevant academic research and scientific papers

ETHYNYLBENZENE DERIVATIVES

Disclosed are compounds of formulae (I), (II), and (II)I: and pharmaceutically acceptable salts thereof, wherein the variables, R, R1, R2, R3, R101, L, D, Q, Y, X, and Z are defined herein. These compounds are useful for treating Gram-negative bacteria infections.

Synthesis of enantiomerically pure 3-fluoromethylthreonines from (S)-1-fluoro-3-tolylsulfinylacetone

The copper(I) catalysed aldol reaction between methyl isocyanoacetate and (S)-3-fluoro-1-(4-methylphenyl)sulfinylacetone affords oxazoline products which, after diastereoisomer separation, give in high yields optically pure 3-fluoromethylthreonine analogues whose absolute and relative configurations have been assigned through X-ray analyses.