101977-83-7Relevant articles and documents
Enantioselective lipase-catalyzed acetylation of β-lactam precursors of carbapenem antibiotics
Bucciarelli, Maria,Davoli, Paolo,Forni, Arrigo,Moretti, Irene,Prati, Fabio
, p. 2489 - 2494 (2007/10/03)
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.
3-(1'-hydroxyethyl)-2-azetidinones from 3-hydroxybutyrates and N-arylaldimines
Georg,Gill,Gerhardt
, p. 3903 - 3906 (2007/10/02)
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