Synthesis of the E and Z isomers of 1,3,4,5,6-penta-O-acetyl-keto-d-fructose (2,4-dinitrophenyl)hydrazone
✍ Scribed by Kazimír Linek; Juraj Alföldi; Štefan Kučár; Tibor Sticzay; Zlatica Novotná; Biserka Kojić-Prodić
- Publisher
- Elsevier Science
- Year
- 1983
- Tongue
- English
- Weight
- 364 KB
- Volume
- 115
- Category
- Article
- ISSN
- 0008-6215
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✦ Synopsis
Hydrazones of some saccharides exhibit significant biological activities. They inhibit nucleo-and proteo-synthesis in tumorous cells' and the growth of bacteria3. Hydrazones of monosaccharides generally crystallize well, and they are useful derivatives for the identification4 and isolation of reducing carbohydrates'.
Much attention has been paid to study of the structure of hydrazones, both cyclic and acyclic. The structure of hydrazones can be determined by several methods. For crystalline compounds, the most convenient method is X-ray crystal-structure analysis. By this method, the cyclic structure of D-arabinose (4-bromophenyl)hydra-
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Reductive cleavage of fully methylated, partially O-carboxymethylated cellulose had previously been shown to produce 4-O-acetyl-1,5-anhydro-2,3,6-tri-O-methyl-, -2-O-(methoxycarbonylmethyl)-3,6-di-O-methyl-, -3-O-(methoxycarbonylmethyl)-2,6-di-O-methyl-, -6-O-(methoxycarbonylmethyl)-2,3-di-O-methyl-
The title hept-I -enitol( 2) reacted with aldehyde methyl(or phenyl)hydrazones in refluxing methanol or butyl acetate to give I-methyl(or phenyl)-5-(penta-O-acetyl-~-~~u~u~f~~-pentitol-l-yl)pyrazoles in good (for I-methylpyrazoles) or moderate yields (for I-phenylpyrazolcs). The 0-deacetylated produ