84208-62-8

Upstream product

• 139111-01-6 (1'R,3S,4R)-3-(benzyloxycarbonylamino)-4-(1'-tert-butyldimethylsilyloxy-ethyl)-azetidin-2-one 
• 139111-02-7 (1'R,3S,4R)-3-(benzyloxycarbonylamino)-4-(1'-hydroxyethyl)-azetidin-2-one 

Downstream Products

• 75666-47-6 (3S,4S)-3-benzyloxycarbonylamino-4-acetoxy-azetidin-2-one 
• 80582-04-3 (3S-trans)-3-[[(phenylmethoxy)carbonyl]amino]-4-methyl-2-azetidinone 

Relevant academic research and scientific papers

β-lactams from ester enolates and silylimines: An enantiospecific synthesis of monocyclic β-lactams

Optically active 3,4-disubstituted azetidin-2-ones have been prepared by annelation of chiral silylimines derived from (S) or (R)-lactaldehyde with the ester enolate of the ethyl 2,2,5,5-tetramethyl-1,2,5-azadisilolidin-1-acetate (STABASE). Oxidation of the hydroxyethyl side chain on the C-4 position of the β-lactam ring, followed by Baeyer-Villiger oxidation led to the optically active (3S, 4S) 3-amino-4-acetoxy-β-lactam. The absolute configuration of this compound was determined by elaboration of this substrate to a key intermediate in the synthesis of the antibiotic 'Aztreonam'. Nucleophilic displacement of the acetoxy group led to optically active 3-amino-4-alkyl(aryl)-azetidin-2-ones.