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Molecules 2000, 5(4), 665-673; https://doi.org/10.3390/50400665

Facile Synthesis of (R,R) and of (R,S) Tricarballylic Acid Anhydride and Imide Derivatives

Department of Chemistry, Faculty of Science, University of Ain Shams, Abbassia 11566, Cairo, Egypt
Received: 17 May 1999 / Revised: 23 March 2000 / Accepted: 3 April 2000 / Published: 15 April 2000
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Abstract

The diastereomeric mixture of (R)-2-(methoxycarbonylmethyl)-N-(R)-1-(1-phenylethyl) succinimide 11s and (S)-2-(methoxycarbonylmethyl)-N-(R)-1-(1-phenylethyl) succinimide 11a was synthesized by reaction of 2-(carboxymethyl)succinic anhydride 6 with (R)-(α)-methylbenzylamine in dry THF/room temperature/24 hrs. The diastereomeric mixture of 1-[(R)-(α)-Methylbenzylamideformyl)]propane-2,3-dicarboxylic acid anhydride 9s and 1-[(R)-(α)-methylbenzylamideformyl)]propane-2,3-dicarboxylic acid anhydride 9a was isolated as an intermediate under the reaction conditions. This diastereomeric mixture 9s/9a was also prepared by a different route via reaction of 1-(chloroformyl)propane-2,3-dicarboxylic acid anydride 12 with (R)-(α)-methylbenzylamine in the presence of DMA at 0oC for 24 hrs. View Full-Text
Keywords: Fumonisin; AAL Toxin TA; Actinoplanic acid; Diastereomers of Tricarballylic acid; Sphingosine analogs Fumonisin; AAL Toxin TA; Actinoplanic acid; Diastereomers of Tricarballylic acid; Sphingosine analogs
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Elgazwy, A.-S.S.H. Facile Synthesis of (R,R) and of (R,S) Tricarballylic Acid Anhydride and Imide Derivatives. Molecules 2000, 5, 665-673.

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