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• 78699-85-1 2,3,4,5,6-penta-O-benzyl-aldehydo-D-glucose 

Relevant academic research and scientific papers

1,3-Dicarbonyl sugar derivatives from sugar nitro-olefins

The sugar nitro-olefins 5-9, easily available from the aldehydo-sugars 1- 4 and simple nitroalkanes, undergo a slow transformation, by treatment in DMF with a mixture of tetrabutylammonium hyrogensulfate (2 mol) and potassium fluoride (4 mol) at room temperature, to give the corresponding enol ethers 10-14, in 10-71% yields, as E/Z mixtures, with the exception of 12, which is configurationally homogenous. The spectroscopic properties of the enol ethers 10-14 are in agreement with their structures. A proof of the potential usefulness of these compounds as equivalent of sugar 1,3-dicarbonyl compounds is the reaction of 12 with hydrazine hydrate, which affords the pyrazole derivative 15 (53%). The formation of 10-14 from 5-9 may be rationalized in terms of a vinylogous Nef-type reaction. Jacobson conditions, as applied to the nitroalkene 7, led to the dimethyl acetal 16 (47%) as a E/Z mixture, which was transformed into the pyrazole denvative 15 in poor yield (14%). This method is therefore less convenient for 7 than the on described here, which seems to be of wider applicability in the carbohydrate field.

Synthesis of Aliphatic 1,3-Dinitro Compounds

Reaction of primary aliphatic nitro compounds with primary or secondary α-nitroalkenes in the presence of catalytic amounts of triethylamine or potassium carbonate affords good yields of 1,3-dinitro compounds.