REACTION OF ETHYL 2-AMINO-4,6-O-BENZYLIDENE-2-DEOXY-D-GLUCONATE WITH ACETYLENIC ESTERS

Article abstract of DOI:10.1016/0008-6215(84)85127-7

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 spectroscopic and chemical methods.