250694-91-8

Upstream product

• 131991-01-0 1<(1',2'-dideoxy-3',4';5',6'-di-O-isopropylidene-1'(1,3-propanedithio))-D-2'-glucosyl>-3β-methoxy-4β-styryl-2-azetidinone 
• 104-55-2 3-phenyl-propenal 
• 109721-80-4 3,4:5,6-di-O-isopropylidene-1,1-bis-ethylsulfanyl-D-glucosamine 
• 135565-73-0 (3S,4R)-1-[(R)-2,2-Bis-ethylsulfanyl-1-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl]-3-methoxy-4-((E)-styryl)-azetidin-2-one 

Downstream Products

• 250694-93-0 (E)-(S)-4-[(3S,4R)-3-Methoxy-2-oxo-4-((E)-styryl)-azetidin-1-yl]-4-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-but-2-enoic acid methyl ester 

Relevant academic research and scientific papers

Stereospecific synthesis of polyfunctionalized carbacephams induced by titanocene(III) chloride

Enantiomerically pure N-substituted epoxyalkene-2-azetidinones reacted with titanocene monochloride to give stereospecifically polyfunctionalized bicyclic β-lactams. Four isomeric epoxyaldehydes 2 reacted with TiCp2- Cl to give exclusively the respective carbacephams 7 while under the same reaction conditions the epoxyesters 1, which are more hindered for an intramolecular addition, gave the cyclization products 6 (only two isomers) and/or the elimination products 5 (all isomers).

A regio and stereospecific synthesis of carbacephem antibiotics

In this article we report a short and practical route to chiral carbacephems 1 based on an asymmetric Staudinger reaction for building the β-lactam ring, and on a tandem elimination-conjugate addition for making the second ring.