3082-92-6

Upstream product

• 100-63-0 phenylhydrazine 
• 50-99-7 D-glucose 
• 108-24-7 acetic anhydride 
• 534-97-4 glucosazone 
• 102918-98-9 3,4,5,6-tetra-O-acetyl-D-lyxo-hexosulose 1-acetylphenylhydrazone 2-phenylhydrazone 

Downstream Products

• 55649-78-0 5-(1,2-dihydroxy-ethyl)-1-phenyl-1H-pyrazole-3-carbaldehyde acetyl-phenyl-hydrazone 
• 1010084-40-8 Acetic acid (S)-2-acetoxy-1-(5-formyl-2-phenyl-2H-pyrazol-3-yl)-ethyl ester 

Relevant academic research and scientific papers

Hydrophilically functionalized pyrazoles from sugars

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.

A CONTRIBUTION TO THE CHEMISTRY OF PYRAZOLE-TYPE DIANHYDROPHENYLOSAZONES

3,4,5,6-Tetra-O-acetyl-D-lyxo-hexosulose 1-acetylphenylhydrazone 2-phenylhydrazone (10) was transformed into 5-(D-glycero-1,2-diacetoxyethyl)-3-formyl-1-phenylpyrazole acetylphenylhydrazone (D-4, n=3) in boiling acetic anhydride containing anhydrous sodiu