Reaction of ethyl 2-amino-4, 6-O-benzylidene-2-deoxy-d-gluconate with acetylenic esters

LMV de Miguel, JAS Blázquez, FJG Barros…

Index: Miquel, Luis M. Vazquez de; Blazquez, Jose A. Serrano; Barros, Fernando J. Garcia; Guillen, Manuel Gomez Carbohydrate Research, 1984 , vol. 126, p. 81 - 90

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Abstract

Abstract Ethyl 2-amino-4, 6-O-benzylidene-2-deoxy-d-gluconate adds to acetylenic esters to give sugar enaminones. The following acetylene derivatives have been employed: methyl propiolate, ethyl phenylpropiolate, and dimethyl acetylenedicarboxylate (6). With compound 6, the reaction leads to a mixture of the expected enaminone and the isomeric oxazolidine derivative. The structures and configurations of the new compounds were studied by ...