Fructose pentaacetate

In all of these processes, it is not clear whether the aluminum chloride, the phosphorus pentachloride, or both are the primary chlorinating agents. While phosphorus pentachloride alone in chloroform has been reported9 to produce tetraacetyl-a-D-fructosyl chloride from /3-D-fructose pentaacetate, its action on /3-D-glucose pentaacetate in the absence of... 

Keto-Fructose Pentaacetate, M. L. Wolfrom and Alva Thompson, J. Amer. Chem. Soc., 56, 880-882 (1934). 

D-Fructose diethyl thioacetal pentaacetate to 2-desoxy-D-glucitol penta- ... 

The major pathway of fragmentation of D-fructose diethyl dithioacetal pentaacetate is connected with production of the U and V series. The series Y and AA are of low intensity, and the Xi fragment is absent. 

Hudson and Brauns87 were the first to prepare crystalline /8-D-fructo-pyranose pentaacetate, m. p. 108-109°, [o]d —120.9° in chloroform. It was obtained in 20% yield by the action of acetic anhydride and sulfuric acid on D-fructose at —15°. This is still the only direct method available for making this compound. The same pentaacetate was obtained by the further acetylation of D-fructose 1,3,4,5-tetraacetate with acetic anhydride and sulfuric acid at —15°. 

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