Carbohydrates isomaltulose

Therefore, taking into account the potentialities of such lactones as carbohydrate delivery synthons (vide infra), several routes leading to carboxymethyl glycosides (and thus subsequently to the lactones) were investigated, in order to get as many structural variations as possible for widening the scope of their use in synthesis. In addition to the isomaltulose oxidation method (route a), the oxidation of allyl glycosides (route b), and the anomeric alkylation with tert-butylbromoacetate (route c) were studied (Scheme 11). These three methods are detailed in the following sections. 

Jarrell, H.C., Conway, T.F., Moyna, P., and Smith, I.C.P., Manifestation of anomeric form, ring structure, and linkage in the carbon-13 NMR spectra of oligomers and polymers containing D-fructose, maltulose, isomaltulose, sucrose, leucrose, 1-kestose, nystose, inulin, and grass levan, Carbohydrate Res., 76, 45-57, 1979. 

Focus is also put on the third pathway which includes reactions of sucrose which lead to carbohydrate structures different from the starting carbohydrate sucrose. This includes the inversion of sucrose to the monomers o-glucose and o-fmctose but also enzymatic rearrangements of the two sucrose building blocks to other carbohydrates, e.g., isomaltulose and trehalulose. 

In an alternative strategy starting from isomaltulose, new carbohydrate containing acrylates were recently prepared by aqueous Baylis-Hillman reaction of a-D-glucosylo>grmethylfurfural 36 with various acrylates was reported (Scheme 14). This new approach towards totally biobased functional compounds (potential monomers, surfactants) appears very attractive when considering that the reaction can take place in water or other media such as water - dimethylisosorbide (DMI) mixtures. 

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