3554-89-0Relevant academic research and scientific papers
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 (1981)
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.
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.
