6983-65-9Relevant 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
Sallam, Mohammed A.E.,Hegazy, Estrwah I.A.,Whistler, Roy L.,Markley, John L.,Croll, David H.
, p. 197 - 206 (2007/10/02)
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
Sallam, Mohammed A. E.,Hegazy, Estrwah I. A.
, p. 177 - 188 (2007/10/02)
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.
STRUCTURE AND ANOMERIC CONFIGURATION OF THE 3,6-ANHYDRO-OSAZONE DERIVATIVES OBTAINED FROM D-lyxo-HEXULOSE PHENYLOSAZONE AND D-xylo-HEXULOSE PHENYLOSAZONE
Sallam, Mohammed A. E.,Hegazy, Estrwah I. A.
, p. 91 - 98 (2007/10/02)
Dehydration of D-lyxo-hexulose phenylosazone or D-xylo-hexulose phenylosazone afforded 3,6-anhydro-D-lyxo-hexulose phenylosazone (2) as the preponderant isomer from both.The identity of 2 was obtained by acetylation, and comparison of the products.Acetylation with acetic anhydride-pyridine afforded the same di-O-acetyl derivative, and further acetylation afforded the same N-acetyldi-O-acetyl derivative (5).Refluxing 2 with copper sulfate afforded a C-nucleoside analog, namely, 2-phenyl-4-α-D-threofuranosyl-1,2,3-osotriazole (6).The anomeric configuratin of 2, 5, and 6 was determined by n.m.r. spectroscopy.The mechanism of the dehydrative cyclization-process, and the conformational stability of 2, are discussed.
