Di-D-fructose dianhydrides derivatives

Optical Rotations and Melting Points of Di-D-fructose Dianhydride Derivatives and Their Per-0-acetates... 

C NMR Spectra of the Fructose Components in Di-D-fructose Dianhydride Derivatives... 

Paper ionophoresis, sugars, Maurice Stacey s work, 17 Pectic acid, 350, 352,414 Pectin, 348, 350-353 Pectinic acid, 353 Pentulose, synthesis, 281 D-cryt/iro-Pentulose 5-phosphate, 289 Peptidoglycans, 167-168 Per-O-acetylated di-D-fructose dianhydride derivatives... 

Similar anomalous distributions are observed in other thermal product mixtures. A commercial soft caramel made by heating sucrose and 0.1% acetic acid to 160°C contained 18% of a mixture of di-D-fructose dianhydrides.94 fi-D-Fru/-1,2 2,1 - 3-D-Fru/(now assigned as a-D-Fru/-l,2 2,l -a-D-Fru/83), ot-D-Fru/-1,2 2,1 -p-D-Fru/(5), ot-D-Frup-1,2 2,l -0-D-Fnjp (4), ot-D-Fru/-l,2 2,1 - 3-D-Frup (1), and p-D-Fru/-l,2 2,3 - 3-D-Fru/ (2) were found in the ratio 4 12 1 6 2. The first three of these, constituting 68% of the mixture, are considered to be kinetic products. The authors commented on this, but did not offer any explanation. Notice, however, that the preparation of such commercial caramels commences with heating of an acidic aqueous solution of sucrose, which almost certainly results in hydrolysis. Hence, the final dianhydrides are probably derived from the reaction of fructose, rather than sucrose. 

The raw materials from which di-D-fructose dianhydrides can be obtained in appreciable yield are readily available from comparatively inexpensive agricultural feedstocks. Thus, these compounds are attractive as chiral-starting materials for chemical synthesis. Their stability to acid and heat, and their relative rigidity, because of the conformational constraints covered here, are also features that might be exploited during syntheses.119 A series of variously substituted di-D-fructose dianhydrides has been prepared,119 starting from 6,6 -dideoxy-6,6 -di-halosucroses. The properties of these and other derivatives of di-D-fructose dianhydrides are summarized in Tables XIV-XX. Two of these derivatives, 48 and 56, exhibit thermotropic liquid-crystal properties.119... 

H NMR Spectra of Fructose Components of Derivatives of Per-0-acetyl Derivatives of Di-D-fructose Dianhydrides... 

Similar instances, in which analytical data were of prime importance and where no products were isolated, are the oxidations of various di-D-fructose dianhydrides,80 inositols,81 the trisaccharide moiety of the alkaloid solamargine,82 2-O-a-L-fucopyranosyl-L-fucitol derived from fucoidin83 (a polysaccharide sulfate ester), trehalose and neotrehalose,84 maltotetraose,85 D-galactopyranosyl-glyceritol,86 and a 3-pentulose.87... 

Other compounds identified in caramels are di-D-fructose and poly(glycosyl) dianhydrides (DFAs). DFAs were found in caramels prepared from D-fructose, D-glucose, and sucrose. The analysis was done after derivatization as TMS (per-0-trimethylsilyl) derivatives or as TMS-oxime (per-O-trimethylsilyl oxime) by... 

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