99530-27-5

Upstream product

• 108-05-4 vinyl acetate 
• 75853-10-0 (+/-)-2-hydroxy-2-(pentafluorophenyl)acetonitrile 
• 653-37-2 perfluorobenzaldehyde 
• 143-33-9 sodium cyanide 
• 75-36-5 acetyl chloride 

Downstream Products

• 271788-76-2 (R)-2-(tert-butyldimethylsilyloxy)-2-(pentafluorophenyl)acetonitrile 
• 615557-66-9 (1R,2S)-2-(tert-butyldimethylsiloxy)-2-(pentafluorophenyl)-1-phenylethylamine 
• 615557-68-1 (1R,2S)-2-amino-1-(pentafluorophenyl)-2-phenylethanol 

Relevant academic research and scientific papers

Lipase-catalyzed transesterification of 2-hydroxy-2- (pentafluorophenyl)acetonitrile leading to (1R,2R)-and (1S,2S)-bis (pentafluorophenyl)ethane-1,2-diol

Optically pure (IR,2R)- and (1S,2S)-1,2-bis(pentafluorophenyl)ethane- 1,2-diol (1) were synthesized from key intermediates (R)- and (S)-2-hydroxy- 2-(pentafluorophenyl)acetonitrile (2), both of which were prepared by the lipase LIP-catalyzed transesterification (E - 465). The absolute configuration of (S)-2 was determined by X-ray structural analysis after transformation into (S)-a-cyano-2,3,4,5,6-pentafluorobenzyl (S)-6-methoxy-a- methyl-2-naphthaleneacetate (S,S)-9. In addition, the crystal structure of (S,S)-9 has an interesting well-ordered packing pattern which shows face-to- face stacking interactions and end-to-end parallel contacts between the pentafluorophenyl and 6-methoxynaphthyl groups of the adjacent molecules.

Lipase-catalyzed kinetic resolution of 2-acyloxy-2- (pentafluorophenyl)acetonitrile

The lipase-catalyzed kinetic resolution of (±)-2-acyloxy-2- (pentafluorophenyl)acetonitrile (±)-1 gave optically active cyanohydrin (S)- 2 and its antipodal ester (R)-1 (E = 211), the former of which was transformed (TBSOTf, DMAP) into its TBS-ether (S)-3, a new fluorinated chiral building block, and into naproxen ester 4 for X-ray analysis to determine the absolute configuration.