New Derivatives of d-Erythronic and l-Erythronic Acid

Chemistry of the Carbohydrates and Glycosides

“…The 1,s-anhydride of 2,3,4,6-tetramethyl glucose-1,2-enediol prepared by Wolfrom & Husted (116) is of con siderable interest because it is the anhydride of the enediol postulated as an intermediate in the alkaline interconversion of tetramethyl glucose and tetramethylmannose (117). In continuation of their studies with barium hydroxide, Upson and his associates (118) have found that the alkaline cleavage of the carbon chain of the aldonic acids containing from two to seven carbon atoms may be explained more satisfactorily by Schmidt's theory that the double bond strength ens the adjacent single bond but weakens the next following bond, than by the enediol theory of Nef. Apparently, the oxidative cleavage of the enediols and the alkaline cleavage of the sugar acids follow quite different courses.…”

Liquid ammonia research in 1938—A review

“…over a period of three days. The amides of d-and /-erythronic acids have been prepared in quantitative yields by the action of liquid ammonia at room temperature on the corresponding lactones (86).…”