3-Oxoglutaric acid diethyl ester

On heating the parent acid of ester VI (from condensation of D-glucose with diethyl 3-oxoglutarate) in aqueous solution,11 following the procedure employed to obtain the corresponding derivative of ethyl acetoacetate XXVI, a sirup results. However, its change in optical activity shows a parallelism with that in analogous cases where crystalline products are isolated, and apparently indicates anhydride formation (see the last line in Table V). 

The reaction, under the same conditions, has been extended to other /3-keto esters. Ethyl 3-oxovalerate, ethyl 3-oxohexanoate, and diethyl 3-oxoglutarate react with 2-amino-2-deoxy-D-glucose to give compounds (11), (12), and (13), respectively, whose oxidations with lead tetraacetate or periodic acid furnish the corresponding aldehydes (14), (IS), and (16). 

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