Cyclic Structures in Sucrose

The discovery, by Purdie and his collaborators, that the reaction between a lower alkyl iodide and the silver salt of a simple hydroxy acid yielded a proportion of the corresponding alkoxy ester, led to the silver 

D-fructofuranoside. The methylation results did not determine the two alpha or beta glycosidic configurations about the biose junction, and XV, like II, therefore had four possible configurations. 

Constitution XV for sucrose has up to the present satisfied all demands made upon it. Like its precursors, I and II (page 6), it was not incompatible with physical properties of sucrose such as the magnetic rotation, or the parachor, although the latter claim has been denied. Von Lippmann lists a great many early determinations of the physical properties of the sugar more recent measurements include the heat of combustion, the molecular weight in liquid ammonia, and various optical and electrical constants.  

The ready condensation of sucrose with excess triphenylmethyl chloride in pyridine to a tri-trityl ether is, however, more easily explained by XV or II, which have three, instead of two (c/. I), primary alcohol groups to react selectively in the condensation. Fleury and Courtois oxidized sucrose for twenty-four hours at 14° with an excess of suitably buffered periodic acid and found that three moles of the oxidant were consumed and one mole of formic acid was eliminated. This highly selective oxidant is known to cleave unsubstituted 1,2 glycols quantitatively to two carbonyl groups and to eliminate the center carbon atom 

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