106847-31-8Relevant articles and documents
Studies on the design and synthesis of new monocyclic β-lactams containing substructures of penicillin G
Lee, Sang Hyup
, p. 2990 - 2994 (2014/12/10)
The studies on design and synthesis of new monocyclic β-lactam esters 4(R/S)-(1′-methoxycarbonylpropyl-2′(R/S)-thio)-3(R)-phenylacetamidoazetidin-2-one (3a) and 4(R/S)-(1′-methoxycarbonyl-2′-methyl-propyl-2′-thio)-3(R)-phenylacetamidoazetidin-2-one (3b) were described. Compounds 3a and 3b were specifically designed to retain all penicillin substructures except the bicyclic system, which would be conceived by cleaving the C(3)-N(4) bond of penicillin G. Compounds 3a and 3b are of particular interest in the context of the structural elucidation of monocyclic β-lactams originated from penicillin. Key intermediates, β-mercapto esters 6a and 6b, were synthesized from conjugate acids 4a and 4b using three-step synthetic sequences, respectively, and 4(S)-acetoxy-3(S)-phenylacetamidoazetidin-2-one (7) was obtained from the degradation of penicillin G. Reactions of 6a and 6b with 7, thus obtained, provided the target compounds 3a and 3b, respectively.
