400009-40-7

Upstream product

• 629648-08-4 (1S,2'R)-1-(1'-benzyloxycarbonyl-4'-oxopiperidin-2'-yl)-2-(tert-butyldimethylsilyloxy)ethylcarbamic acid tert-butyl ester 
• 629648-04-0 (6S)-7-(tert-butyldimethylsilyloxy)-6-(tert-butoxycarbonylamino)-1-(p-toluenesulfonyl)-4-hepten-3-one 
• 629648-06-2 (4S,2'R)-4-(1'-benzyloxycarbonyl-4'-oxopiperidin-2'-yl)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidine 
• 629648-03-9 (4S)-4-[3-oxo-5-(4'-methylphenylsulfonyl)-1-pentenyl]-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidine 
• 100-46-9 benzylamine 
• 124085-68-3 tert-butyl (R)-1-(tert-butyldimethylsilyloxy)-3-oxopropan-2-yl carbamate 
• 95715-87-0 (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine 
• 629648-09-5 (1S,2'R)-1-(1'-benzyloxycarbonyl-4'-oxopiperidin-2'-yl)-2-(hydroxy)ethylcarbamic acid tert-butyl ester 

Downstream Products

• 400009-41-8 (2S,2'R)-tert-butoxycarbonylamino-(4'-oxopiperidin-2'-yl)-acetic acid 

Relevant academic research and scientific papers

Diastereoselective synthesis of 2-substituted-piperidin-4-ones as convenient precursors for an asymmetric approach to carbacephams

Optically active carbacephams can be efficiently prepared generating the β-lactam ring on 2-substituted-piperidin-4-ones. These can, in turn, be prepared diastereoselectively through a Michael-Michael reaction sequence initiated by benzylamine on precursors derived by Wittig reaction between serinals and 4-[(4-methylphenyl)sulfonyl]-1-(triphenylphosphoranylidene)-2-butanone.

Asymmetric hetero Diels-Alder as an access to carbacephams

A short and efficient asymmetric synthesis of the (6R,7S)-7-tert-butoxycarbonylamino-2-ketocarbacepham is described. The key step involves the hetero Diels-Alder reaction of the benzylimine derived from the enantiomer of Garner's aldehyde with Danishefsky's diene.