79726-78-6

Basic information

• Product Name: 4-(2,3-O-isopropylidene-β-D-erythrofuranosyl)-2-phenyl-1,2,3-triazole
• CAS NO: 79726-78-6
• Molecular Weight: 287.318
• Mol File: 79726-78-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4-(2,3-O-isopropylidene-β-D-erythrofuranosyl)-2-phenyl-1,2,3-triazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2,3-O-isopropylidene-β-D-erythrofuranosyl)-2-phenyl-1,2,3-triazole(79726-78-6)
• EPA Substance Registry System: 4-(2,3-O-isopropylidene-β-D-erythrofuranosyl)-2-phenyl-1,2,3-triazole(79726-78-6)

Safety Data

• Hazardous Substances Data: 79726-78-6(Hazardous Substances Data)

Upstream product

• 67-64-1 acetone 
• 18402-97-6 α-D-erythrofuranosyl-2-phenyl-2H-1,2,3-triazole 
• 77-76-9 2,2-dimethoxy-propane 
• 6341-06-6 2-phenyl-4-(D-arabino-1',2',3',4'-tetrahydroxybutyl)-2H-1,2,3-triazole 
• 188964-33-2 β-D-erythrofuranosyl-2-phenyl-2H-1,2,3-triazole 
• 205990-41-6 D-(1S)-1-(2-phenyl-2H-[1,2,3]triazol-4-yl)-erythritol 
• 1990-29-0 D-altrose 
• 52387-26-5 D-ribose cyanohydrin 
• 35522-78-2 3,6-anhydro-D-ribo-hexulose henylosazone 
• 534-97-4 D-ribo-hexulose phenylosazone 

Relevant articles and documents

Studies on epimeric-D-arabino- and -D-ribo-tetritol-1-yl-2-phenyl-2 h- 1,2,3-triazoles. Synthesis and anomeric configuration of 4-(α- and β-D- erythrofuranosyl)-2-phenyl-2 h-1,2,3-triazole C-nucleoside analogs

Treatment of 4-(D-arabino-tetritol-l-yl)-2-phenyl-2 H-1,2,3-triazole (1) with one mole equivalent of tosyl chloride in pyridine solution, afforded the C-nucleoside analogs, 4-(α-D-erythrofuranosyl)-2-phenyl-2 H- 1,2,3-triazole (2) in 25% yield, as well as the byproduct 4-(4-chloro-4-deoxy-D-arabino- tetritol-l-yl)-2-phenyl-2 H-1,2,3-triazole(3). Treatment of the epimeric 4- (D-ribo-tetritol-l-yl)-2-phenyl-2 H-1,2,3-triazole(8) with tosyl chloride in pyridine solution afforded the anomeric C-nucleoside analogs, 4-(β-D- erythrofuranosyl)-2-phenyl-2 H-1,2,3-triazole (9) in 23% yield. Similar treatment of 8 with trifluoromethanesulfonyl chloride in pyridine solution afforded 9. The structure and anomeric configuration of these compounds were determined by acylation, NMR, NOE, circular dichroism spectroscopy and mass spectrometry.

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.