Stereoselective Synthesis of a New cis Monocyclic β-lactam Bearing a Sugar Moiety at Its N1 Position and Its Physical Characterization

Molbank

关键词: 2-azetidinone;    phenoxy ketene;    asymmetric synthesis;    chiral Schiff bases;    sugar;    [2+2] cycloaddition;   

DOI  :  10.3390/M544

来源: DOAJ

【 摘 要 】

Synthesis of a new monocyclic β-lactam containing a sugar moiety at its N1 position via [2+2] cycloaddition reaction of ketene and imine is described. Reaction of achiral phenoxy ketene with chiral aldimine derived from chiral 2, 3, 4, 6-tetra-O-acetyl-β-D-galactopyranosylamine and 2-hydroxy-3-methoxy benzaldehyde resulted in the formation of 2 as a single diastereomer. Then its physical characterization has been determined at the AM1 level of theory.