Abstract
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.
Highlights
O-Acyl-protected glycosylamines and their imine derivatives, the 2,3,4,6-tetra-O-pivaloylD-galactopyranosylamine and its acetyl derivative are effective chiral auxiliaries in Strecker and Ugi syntheses of α-amino acids [1,2,3]
In this paper a new sugar based monocyclic 2-azetidinone has been synthesized as a single diastereomer based on asymmetric synthesis and its physical characterization has been determined at the AM1 level of theory
D-(+)-Galactose was chosen as the starting material for the synthesis of β-D-galactosylamine. 2, 3, 4, 6-Tetra-O-acetylβ-D-galactopyranosyl bromide was readily displaced by an azido group
Summary
O-Acyl-protected glycosylamines and their imine derivatives, the 2,3,4,6-tetra-O-pivaloylD-galactopyranosylamine and its acetyl derivative are effective chiral auxiliaries in Strecker and Ugi syntheses of α-amino acids [1,2,3]. Introduction O-Acyl-protected glycosylamines and their imine derivatives, the 2,3,4,6-tetra-O-pivaloylD-galactopyranosylamine and its acetyl derivative are effective chiral auxiliaries in Strecker and Ugi syntheses of α-amino acids [1,2,3]. The asymmetric Staudinger reaction utilizing 2,3,4,6-tetra-O-acetylβ-D-galactopyranosylimine or 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylimine as the chiral auxiliary in the synthesis of 2-azetidinones has been reported by us [8] and others [9].
Sign-in/Register to view highlights & summary Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
