35522-79-3

Upstream product

• 534-97-4 glucosazone 
• 100-63-0 phenylhydrazine 
• 103421-22-3 3,6-Anhydro-D-mannose 
• 59-88-1 phenylhydrazine hydrochloride 
• 7625-23-2 3,6-anhydro-D-glucose 
• 6164-71-2 D-allose osazone 
• 3056-46-0 methyl 3,6-anhydro-β-D-glucopyranoside 
• 164199-92-2 D-arabino-hexulose phenylosazone 
• 534-97-4 D-ribo-hexulose phenylosazone 
• 1990-29-0 D-altrose 
• 534-97-4 L-lyxo-hexulose phenylosazone 
• 534-97-4 L-xylo-2-hexulose phenylosazone 
• 52387-26-5 D-ribose cyanohydrin 

Downstream Products

• 101148-46-3 1-phenylazo-D-arabino-3,6-anhydro-[2]hexosulose-bis-phenylhydrazone 
• 188964-32-1 di-O-acetyl-D-arabino-3,6-anhydro-[2]hexosulose-bis-phenylhydrazone 
• 18402-97-6 α-D-erythrofuranosyl-2-phenyl-2H-1,2,3-triazole 
• 81872-42-6 2-phenyl-4-α-L-threofuranosyl-1,2,3-osotriazole 
• 188964-33-2 β-D-erythrofuranosyl-2-phenyl-2H-1,2,3-triazole 
• 75869-72-6 4,5-O-isopropylidene-β-D-erythro-hexulofuranose bis(phenylhydrazone) 
• 79726-78-6 4-(2,3-O-isopropylidene-β-D-erythrofuranosyl)-2-phenyl-1,2,3-triazole 
• 78077-10-8 4,5-di-O-acetyl-3,6-anhydro-L-lyxo-2-hexulose phenylosazone 
• 3554-89-0 N-acetyl-4,5-di-O-acetyl-3,6-anhydro-L-lyxo-hexulose phenylosazone 
• 75869-73-7 C₃₄H₃₀N₁₀O₃ 

Relevant academic research and scientific papers

STUDIES ON 3-EPIMERIC L-2-HEXULOSE PHENYLOSAZONES. STRUCTURE AND ANOMERIC CONFIGURATION OF THE 3,6-ANHYDRO-OSAZONE DERIVATIVES OBTAINED FROM L-xylo- AND L-lyxo-2-HEXULOSE PHENYLOSAZONE

Dehydration of the 3-epimeric 2-hexulose phenylosazones L-xylo-hexulose phenylosazone and L-lyxo-hexulose phenylosazone afforded 3,6-anhydro-L-lyxo-2-hexulose phenylosazone (2) as the preponderant isomer from both.The identity of 2 was obtained by t.l.c., and by acetylation followed by comparison of the products.Acetylation of 2 with acetic anhydride-pyridine afforded the di-O-acetyl derivative 4, and further acetylation gave the N-acetyl-di-O-acetyl derivative 5.Refluxing of 2 with copper sulfate afforded a C-nucleoside analog, namely, 2-phenyl-4-α-L-threo-furanosyl-1,2,3-osotriazole (6).The anomeric configuration was determined by n.m.r. spectroscopy.The stereochemical course of the dehydration process and the mass spectra of compounds 2, 4, 5, and 6 are discussed.

STUDIES ON 3-EPIMERIC 2-HEXULOSE PHENYLOSAZONES. STRUCTURE AND ANOMERIC CONFIGURATION OF THE 3,6-ANHYDRO-OSAZONE DERIVATIVES OBTAINED FROM D-arabino- AND D-ribo-2-HEXULOSE PHENYLOSAZONE

Dehydration of the 3-epimeric 2-hexulose phenylosazones D-arabino-hexulose phenylosazone or D-ribo-hexulose phenylosazone afforded 3,6-anhydro-D-ribo-hexulose phenylosazone (4) as the preponderant isomer from both.The identity of 4 was obtained by t.l.c., and by acylation followed by comparison of the products.Prolonged acetylation with acetic anhydride-pyridine, or by refluxing with acetic anhydride, afforded the same N-acetyldi-O-acetyl derivative.Refluxing 4 with copper sulfate, or the osotriazole with 20percent methanolic sulfuric acid, afforded the C-nucleoside analog, namely, 4-β-D-erythrofuranosyl-2-phenyl-1,2,3-osotriazole (7).The anomeric configurations of 4 and 7 were ascertained from the n.m.r. spectra of their isopropylidene derivatives.The mechanism of the dehydrative cyclization process and the mass spectra of two compounds were discussed.