Carbohydrate Research p. 177 - 188 (1981)
Update date:2022-08-04
Topics:
Sallam, Mohammed A. E.
Hegazy, Estrwah I. A.
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.
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Doi:10.1021/jo00318a037
(1981)Doi:10.1002/hlca.19800630507
(1980)Doi:10.1016/S0040-4039(01)90511-8
(1981)Doi:10.1023/B:COHC.0000044580.94570.18
(2004)Doi:10.1007/s12039-012-0331-4
(2012)Doi:10.1016/j.bmcl.2004.06.051
(2004)