100239-17-6

Upstream product

• 5405-41-4 ethyl 3-hydroxybutyrate 
• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 56816-01-4 ethyl (S)-3-hydroxybutyrate 
• 80542-40-1 N-cinnamylidene-p-anisidine 

Downstream Products

• 205518-58-7 Acetic acid (2R,3S,6S)-2-acetoxymethyl-6-{(R)-1-[(3R,4S)-1-(4-methoxy-phenyl)-2-oxo-4-phenyl-azetidin-3-yl]-ethoxy}-3,6-dihydro-2H-pyran-3-yl ester 
• 146924-91-6 (-)-cis-(3S,4R)-3-hydroxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone 
• 146924-95-0 (-)-(3S,4R)-3-acetoxy-1-(4-methoxyphenyl)-4-phenylazetidin-2-one 
• 106399-74-0 (3S,4R)-3-((S)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-phenyl-azetidin-2-one 
• 205518-66-7 3-keto-4-phenyl-N-p-anisyl-2-azetidinone 
• 205518-65-6 (R)-3-Eth-(Z)-ylidene-1-(4-methoxy-phenyl)-4-phenyl-azetidin-2-one 
• 205518-61-2 (3R,4S)-3-((R)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-phenyl-azetidin-2-one 
• 1198298-98-4 C₂₈H₃₁NO₈ 

Relevant academic research and scientific papers

Enantiomerically pure β-lactams with the thienamycin side chain via glycosylation

Dedicated to the memory of Prof. Shun-ichi Yamada Easy access to both enantiomers of β-lactams with the thienamycin side chain was achieved via iodine catalyzed Ferner reaction with commercially available tri-O-acetyl-D-glucal.

Asymmetric Synthesis of (1'R,3R,4R)-4-Acetoxy-3(1'-((tert-butyldimethylsilyl)oxy)ethyl)-2-azetidinone and Other 3-(1'-Hydroxyethyl)-2-azetidinones from (S)-(+)-Ethyl 3-Hydroxybutanoate: Formal Total Synthesis of (+)-Thienamycin

The synthesis of (1'R,3R,4R)-4-acetoxy-3-(1'-((tert-butyldimethylsilyl)oxy)ethyl)-2-azetidinone, an important precursor for synthesis of carbapenems and penems, is detailed.The methodology utilized relies on the addition, cyclization reaction between the dianion of (S)-(+)-ethyl 3-hydroxybutanoate and N-arylaldimines.The syntheses of other useful optically active 3-(hydroxyethyl)-2-azetidinones are presented.A study of factors influencing the stereochemistry in the addition, cyclization reaction for the formation of 3-(1'-hydroxyethyl)-2-azetidinones is detailed.

3-(1'-hydroxyethyl)-2-azetidinones from 3-hydroxybutyrates and N-arylaldimines

Dianion imine addition, cyclisation reaction between ethyl-3-hydroxybutyrate and the aldimines generates β-lactams with the hydroxyethyl side chain of thienamycin and related β-lactam antibiotics in place. The effects of the N-arylaldimine and the reactio