81748-28-9Relevant academic research and scientific papers
Homo-C-nucleoside analogs III. Studies on the base-catalyzed dehydrative cyclization of 4-(d-manno-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole
Sallam, Mohammed A.E.
experimental part, p. 2233 - 2238 (2010/11/19)
Treatment of 4-(d-manno-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole with one molar equivalent of 2,4,6-triisopropylbenzenesulfonyl chloride (TIBSCl) in pyridine solution afforded the homo-C-nucleoside analog; 4-(2,5-anhydro-d-manno- pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole in 54% yield and 4-(α-d- arabinopyranosyl)-2-phenyl-2H1,2,3-triazole analog in 3% yield. The 4-(5-O-triisopropylbenzenesulfonyl)-d-manno-pentitol-1-yl)-2-phenyl-2H-1,2, 3-triazole analog was isolated as an intermediate and identified as its tetra-O-acetyl derivative. The 4-(5-chloro-5-deoxy-d-manno-pentitol-1-yl)-2- phenyl-2H-1,2,3-triazole analog was isolated as a byproduct. The structure and anomeric configuration of the products were determined by acylation, NMR spectroscopy, and mass spectrometry.
Studies on Anhydro-osazones. Part 5. Structure and Anomeric Configuration of the C-Nucleoside Analogues Obtained from the Dehydration of D-gluco- and D-manno-Hept-2-ulose Phenylosazones
Sallam, Mohammed A. E.
, p. 557 - 562 (2007/10/02)
Dehydration of D-gluco- and D-manno-hept-2-ulose phenylosazones with methanolic sulphuric acid afforded the anomeric furanosyl anhydro-osazone pair: 3,6-anhydro-D-manno-hept-2-ulose phenylosazone (2) and the gluco-analogue osazone (3).A new type of anomeric pyranosyl anhydro-osazone was also idenified.Refluxing the anhydro-osazones with copper sulphate afforded the anomeric furanosyl C-nucleoside analogues 4-α-D-arabinofuranosyl-2-phenyl-v-triazole (6) and the β-isomer (7), and the arabinofuranosyl isomers (8) and (9).The structures and anomeric configurations of the products were determined by periodate oxidation, o.r.d., and n.m.r. spectroscopy.The mechanism of the dehydration and the mass spectra of compounds (6)-(9) are discussed.
