81713-49-7Relevant articles and documents
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.