Carbohydrate Research p. 129 - 142 (1985)
Update date:2022-08-11
Topics:
Perez, Juan A. Galbis
Caballero, Reyes Babiano
Ventula, Arturo Cert
The reaction of 2-amino-2-deoxy-D-glycero-D-altro-heptose hydrochloride with acyclic and cyclic 1,3-dicarbonyl compounds gives, respectively, (D-allo-pentitol-1-yl)-pyrroles and -tetrahydroindoles that can be dehydrated to yield D-ribo-C-glycosyl heterocycles having furanoid or pyranoid structures, depending on the reaction conditions.Thus, when the reactions were kinetically controlled, α- and β-D-ribofuranosyl heterocycles were obtained, but α- and β-D-ribopyranosyl heterocycles were formed under conditions of thermodynamic control.A criterion is proposed to differentiate between both structures on the basis of the mass spectra of their triacetates.
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