956428-49-2

Upstream product

• 56522-24-8 tert-butyldimethylsilyl cyanide 
• 148968-08-5 (+)-(3R,4R)-1-(p-anisyl)-3-benzyloxy-4-formyl-2-azetidinone 
• 180062-99-1 3-methoxy-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carbaldehyde 

Downstream Products

• 956428-59-4 (+)-(3R,4R)-4-((1R)-2-amino-1-[tert-butyl(dimethyl)silyloxy]ethyl)-3-methoxy-1-(4-methoxyphenyl)azetidin-2-one 
• 956428-69-6 (+)-(2S,3R,4R)-2-[tert-butyl(dimethyl)silyloxy]-5-hydroxy-4-methoxy-3-[(4-methoxyphenyl)amino]pentanenitrile 
• 887363-25-9 (+)-(2S)-hydroxy[(2S,3R)-3-methoxy-1-(4-methoxyphenyl)-4-oxoazetidin-2-yl]acetonitrile 
• 956428-91-4 methyl (+)-(2R,3R,4S)-4-[tert-butyl(dimethyl)silyloxy]-4-cyano-2-methoxy-3-[(4-methoxyphenyl)amino]butanoate 
• 956428-97-0 methyl (-)-{(3R,4R,5S)-3-[tert-butyl(dimethyl)silyl]oxy-5-methoxy-4-[(4-methoxyphenyl)amino]piperidin-1-yl}acetate 
• 956428-93-6 (-)-(3R,4R,5R)-5-[tert-butyl(dimethyl)silyl]oxy-3-methoxy-4-[(4-methoxyphenyl)amino]piperidin-2-one 

Relevant academic research and scientific papers

Direct synthesis of protected enantiopure 5-cyano-3,4-dihydroxypyrrolidin- 2-ones from β-lactam aldehydes catalyzed by iodine

A single-step catalytic ring-expansion approach from 4-oxoazetidine-2- carbaldehydes to protected enantiopure 5-cyano-3,4-dihydroxypyrrolidin-2-ones has been achieved by the use of the commercially available and inexpensive reagent, molecular iodine, in the presence of tert-butyldimethyl cyanide. Interestingly, the catalyst directs the reaction toward the selective rearrangement reaction of the β-lactam nucleus rather than cyanohydrin formation. Georg Thieme Verlag Stuttgart.

Stereocontrolled access to orthogonally protected anti,anti-4- aminopiperidine-3,5-diols through chemoselective reduction of enantiopure β-lactam cyanohydrins

(Chemical Equation Presented) The cyanosilylation of enantiopure 4-oxoazetidine-2-carbaldehydes with tert-butyldimethylsilyl cyanide was promoted by either molecular sieves or catalytic amount of sodium carbonate to give O-silylated β-lactam cyanohydrins