102129-92-0Relevant 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.
AN ENANTIOSELECTIVE APPROACH TO CARBAPENEM ANTIBIOTICS: FORMAL SYNTHESIS OF (+)-THIENAMYCIN
Hart, David J.,Ha, Deok-Chan
, p. 5493 - 5496 (2007/10/02)
An enantioselective synthesis of intermediates in synthesis of thienamycin (15) and epithienamycin-C (16) is described.