3082-94-8Relevant academic research and scientific papers
Hydrophilically functionalized pyrazoles from sugars
Oikawa, Nobuhiro,Mueller, Christoph,Kunz, Markwart,Lichtenthaler, Frieder W.
, p. 269 - 279 (1998)
An effective and convenient protocol has been developed for the conversion of D-glucose and 6-O-α-D-glucopyranosyl-D-fructose (palatinose, isomaltulose) into 5-[(1'S)-1','2/-dihydroxyethyl]-1-phenylpyrazole-3-carboxaldehyde (4) and 5-[(1'S)-2-(α-D-glucopyranosyloxy)-1-hydroxethyl])-1-phenylpyrazole-3 -carboxaldehyde (5), key steps being the acetic anhydride-promoted dehydrative cyclization of the respective phenylosazones, and subsequent liberation of the N-acetylphenylhydrazone-blocked aldehyde function. Exploitation of the ensuing chemistry of 4 and 5 led to a variety of pyrazole building blocks with a diverse level of hydrophilic substituents (hydroxymethyl, dihydroxyethyl or glucosyl residues) and useful functional groups, such as chloro, cyano, aminomethyl, vinyl and acryloyl moieties.
