277334-49-3

Upstream product

• 217488-44-3 allyl 1-benzyl-3-oxo-4-piperidinecarboxylate 
• 76899-07-5 (3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one 
• 39514-19-7 ethyl 1-benzyl-3-oxo-4-piperidinecarboxylate 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 277334-45-9 (3S,4R)-4-[4-(allyloxycarbonyl)-1-benzyl-3-oxopiperidin-4-yl]-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone 

Downstream Products

• 217488-46-5 (3R,4S)-4-[(R)-1-benzyl-3-oxopiperidin-4-yl]-1-(tert-butyldimethylsilyl)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone 

Relevant academic research and scientific papers

Stereocontrolled synthesis of piperidine-condensed tricyclic carbapenems (5-azatrinems) and their antibacterial activities

Stereocontrolled synthesis of tricyclic carbapenem (5-azatrinem) derivatives 4, in which a piperidine ring is condensed to the carbapenem skeleton, was achieved. The pivotal tricyclic intermediate 2, allyl (8S,9R,10S)-5-(tert-butoxycarbonyl)-10-[(R)-1-(tert- butyldimethylsilyloxy)ethyl)-11-oxo-1,5-diazatricyclo[7.2.0.03,8]undec-2- ene-2-carboxylate, was synthesized starting from an acetoxyazetidinone chiron 6 in a practical manner based on a C-C bond formation reaction between 6 and piperidinone-ester 5, palladium-catalyzed de(allyloxy)carbonylation of 7b and Wittig-type cyclization via an oxalimide 9. Selective deprotection of the N- Boc group of 2 was found to proceed smoothly by treatment with trimethylsilyl trifluoromethanesulfonate and 2,6-lutidine to give the amino compound 3, whose functionalization on the nitrogen atom to derivatives 10 followed by deprotection led to various 5-azatrinem acids 4. These compounds showed potent in vitro activities against gram-positive and gram-negative bacteria.