Heterocyclic N-glycosyl derivatives—XIII: Reaction of 6-chloropurine and benzotriazoles with acetylated glycals |
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Authors: | M FuertesG García-Mun˜oz FG De Las HerasR Madronero M Stud |
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Institution: | Instituto de Qui´mica Orga´nica General, Departamento de Qui´mica Me´dica, Juan de la Cierva, 3, Madrid -6, Spain; Instituto de Qui´mica-Fi´sica “Rocasolano”, Serrano, 119, Madrid -6, Spain |
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Abstract: | Acid-catalysed reactions of tri-O-acetyl-D-glucal with benzotriazole, 5,6-dimethylbenzotriazole, 5,6-dichlorobenzotriazole and 6-chloropurine have been found to give anomeric mixtures of the corresponding 2′,3′-unsaturated N-glycosyl derivatives with the α-anomers preponderating. When tri-O-acetyl-D-galactal was used the 3′,4′,6′-tri-O-acetyl-α- and β-D-lyxo-hexopyranosyl nucleoside analogs were obtained. The conformation and anomeric configuration of all the N-glycosyl compounds obtained were assigned by NMR studies. |
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