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

Molbank

Aliasghar Jarrahpour¹  Abraham F. Jalbout¹ 

[1] ¹Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran ²Department of Chemistry, University of Arizona, Tucson, AZ 85721 USA

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

DOI  :  10.3390/M544

来源: mdpi

【 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.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.