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

doi:10.3390/M544

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Molbank 2007, 2007(3), M544; doi:10.3390/M544

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

Aliasghar Jarrahpour^1,* , Abraham F. Jalbout² and Parvaneh Alvand¹

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

* Author to whom correspondence should be addressed.

Received: 29 December 2006 / Accepted: 27 February 2007 / Published: 30 May 2007

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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.

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

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Cite This Article

MDPI and ACS Style

Jarrahpour, A.; Jalbout, A.F.; Alvand, P. Stereoselective Synthesis of a New cis Monocyclic β-lactam Bearing a Sugar Moiety at Its N1 Position and Its Physical Characterization. Molbank 2007, 2007, M544.

AMA Style

Jarrahpour A, Jalbout AF, Alvand P. Stereoselective Synthesis of a New cis Monocyclic β-lactam Bearing a Sugar Moiety at Its N1 Position and Its Physical Characterization. Molbank. 2007; 2007(3):M544.

Chicago/Turabian Style

Jarrahpour, Aliasghar; Jalbout, Abraham F.; Alvand, Parvaneh. 2007. "Stereoselective Synthesis of a New cis Monocyclic β-lactam Bearing a Sugar Moiety at Its N1 Position and Its Physical Characterization." Molbank 2007, no. 3: M544.

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