21090-79-9Relevant academic research and scientific papers
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.
STRUCTURE AND ANOMERIC CONFIGURATION OF THE 3,6-ANHYDRO-OSAZONE DERIVATIVES OBTAINED FROM D-altro-2-HEPTULOSE PHENYLOSAZONE
Sallam, Mohammed A. E.
, p. 139 - 148 (2007/10/02)
Dehydration of D-altro-2-heptulose phenylosazone with methanolic sulfuric acid afforded two 3,6-anhydro-osazone derivatives (2 and 3).Compound 3 was obtained as the preponderant isomer, with inversion at C-1 (C-3 of the starting osazone), and 2 was obtained without inversion.Refluxing of 3 with copper sulfate afforded the C-nucleoside analog, namely, 2-phenyl-4-β-D-ribofuranosyl-1,2,3-osotriazole (4).Acetylation of 4 afforded the tri-O-acetyl derivative 5.The anomeric configuration was determined by c.d. and n.m.r. spectroscopy.The mass spectra of compounds 2-5 are discussed.
STUDIES ON ANHYDRO-OSAZONES. STRUCTURE AND ANOMERIC CONFIGURATION OF THE 3,6-ANHYDRO-OSAZONE DERIVATIVES OBTAINED FROM D-galacto-2-HEPTULOSE PHENYLOSAZONE
Sallam, Mohammed A.E.
, p. 93 - 106 (2007/10/02)
Dehydration of D-galacto-2-heptulose phenylosazone with methanolic sulfuric acid afforded two 3,6-anhydro osazone derivatives (2 and 3).Compound 2 was obtained as the preponderant isomer, without inversion at C-1 (C-3 of the starting osazone), and 3 was o
2-phenyl-1,2,3-osotriazole C-nucleoside analogs synthesis and determination of anomeric configuration
Sallam, Mohammed A.E.
, p. 183 - 186 (2007/10/02)
A series of anomeric 2-phenyl-1,2,3-osotriazole C-nucleoside analogs has been prepared. The anomeric configuration was determined by a novel method from the chemical shift of the C-5 proton of the osotriazole base moieties.
