102129-92-0

Upstream product

• 56816-01-4 ethyl (S)-3-hydroxybutyrate 
• 80542-40-1 N-cinnamylidene-p-anisidine 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 88315-63-3 (E)-4-methoxy-N-((E)-3-phenylallylidene)aniline 
• 100009-52-7 3-(1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one 
• 15286-52-9 N-(4-Methoxyphenyl)-3-phenylpropenaldimine 
• 100009-52-7 (3S,4R)-3-((S)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-styryl)-azetidin-2-one 

Relevant academic research and scientific papers

Enantioselective lipase-catalyzed acetylation of β-lactam precursors of carbapenem antibiotics

The Amano PS-lipase-catalyzed enantioselective acetylation in vinyl acetate of (±)-3-hydroxyethyl-β-lactams 3-6, useful precursors of carbapenem antibiotics, proceeds with high enantioselectivity (E > 98) to afford the corresponding acetates 3b-6b in optically pure form. The rate of acetylation is influenced by the relative stereochemistry of the C(3)-C(4) β-lactam carbon atoms, the trans isomers being transformed much faster than the cis ones. The stereochemical preference of the lipase-PS is for the (1′R,3R) enantiomers, as determined by chemical correlation. On the other hand, the lipase-PS-catalyzed hydrolysis of esters 3b,d in phosphate buffer proceeds with low selectivity and at a lower rate.

Preparation of Aminosaccharides Using Ester-Imine Condensations: Syntheses of Methyl N-Benzoylacosaminide and Methyl N-(Oxo(phenylmethoxy)acetyl)daunosaminide from (S)-Ethyl 3-Hydroxybutyrate

The dianion of (S)-ethyl β-hydroxybutyrate (1) was treated with N-trimethylsilyl imine 2 to afford β-lactam 4.The same dianion reacted with N-aryl imine 10 to give β-lactams 11, 12, and 13.A three-step sequence was used to convert 4 into the β-lactam-pyra

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

AN ENANTIOSELECTIVE APPROACH TO CARBAPENEM ANTIBIOTICS: FORMAL SYNTHESIS OF (+)-THIENAMYCIN

An enantioselective synthesis of intermediates in synthesis of thienamycin (15) and epithienamycin-C (16) is described.